HU209283B - Process for producing e-oxime ethers of phenylglyoxylic acid esters - Google Patents
Process for producing e-oxime ethers of phenylglyoxylic acid esters Download PDFInfo
- Publication number
- HU209283B HU209283B HU914162A HU416291A HU209283B HU 209283 B HU209283 B HU 209283B HU 914162 A HU914162 A HU 914162A HU 416291 A HU416291 A HU 416291A HU 209283 B HU209283 B HU 209283B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- acid
- methyl
- och3
- och
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 61
- FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical class OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 245
- 239000000203 mixture Substances 0.000 claims abstract description 74
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- YKNORODREYVARM-UHFFFAOYSA-N 2-(phenoxymethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1COC1=CC=CC=C1 YKNORODREYVARM-UHFFFAOYSA-N 0.000 claims abstract description 32
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 30
- 150000002367 halogens Chemical class 0.000 claims abstract description 30
- 238000002360 preparation method Methods 0.000 claims abstract description 26
- 150000002596 lactones Chemical class 0.000 claims abstract description 19
- 229940031826 phenolate Drugs 0.000 claims abstract description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 claims abstract description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 159
- 239000002253 acid Substances 0.000 claims description 124
- -1 alkaline earth metal cyanide Chemical class 0.000 claims description 87
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 55
- 239000011541 reaction mixture Substances 0.000 claims description 31
- 239000006227 byproduct Substances 0.000 claims description 19
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 239000002585 base Substances 0.000 claims description 18
- 239000003085 diluting agent Substances 0.000 claims description 18
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 150000001408 amides Chemical class 0.000 claims description 14
- GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 claims description 12
- 150000002989 phenols Chemical class 0.000 claims description 12
- JEVCFPPYJUBGIO-UHFFFAOYSA-N 2-(phenoxymethyl)benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1COC1=CC=CC=C1 JEVCFPPYJUBGIO-UHFFFAOYSA-N 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- MIGNJKDTMBBNFI-UHFFFAOYSA-N 2-(phenoxymethyl)benzoyl cyanide Chemical compound N#CC(=O)C1=CC=CC=C1COC1=CC=CC=C1 MIGNJKDTMBBNFI-UHFFFAOYSA-N 0.000 claims description 9
- 230000002140 halogenating effect Effects 0.000 claims description 9
- 239000000155 melt Substances 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
- WWKJGJMTJOIBJW-UHFFFAOYSA-N methyl 2-oxo-3-phenoxypropanoate Chemical class COC(=O)C(=O)COC1=CC=CC=C1 WWKJGJMTJOIBJW-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims 1
- 150000002148 esters Chemical class 0.000 abstract description 47
- 125000001424 substituent group Chemical group 0.000 abstract description 25
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 21
- GJQBHOAJJGIPRH-UHFFFAOYSA-N benzoyl cyanide Chemical compound N#CC(=O)C1=CC=CC=C1 GJQBHOAJJGIPRH-UHFFFAOYSA-N 0.000 abstract description 21
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract description 15
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 7
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 abstract 1
- 150000004716 alpha keto acids Chemical class 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 864
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 270
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 195
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 87
- 238000006243 chemical reaction Methods 0.000 description 74
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 68
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- 239000000460 chlorine Substances 0.000 description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
- 239000000243 solution Substances 0.000 description 43
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 37
- 239000002904 solvent Substances 0.000 description 37
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 33
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 150000007513 acids Chemical class 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 20
- SLVQLQSCRLIDRC-UHFFFAOYSA-N 2-[(2-methylphenoxy)methyl]benzoyl cyanide Chemical compound CC1=CC=CC=C1OCC1=CC=CC=C1C(=O)C#N SLVQLQSCRLIDRC-UHFFFAOYSA-N 0.000 description 19
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 19
- 239000012043 crude product Substances 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 16
- 229910052801 chlorine Inorganic materials 0.000 description 16
- 239000007789 gas Substances 0.000 description 16
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 16
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 15
- 239000011737 fluorine Substances 0.000 description 15
- 229910052731 fluorine Inorganic materials 0.000 description 15
- DVQZMPYYTUUGAK-UHFFFAOYSA-N methyl 2-[2-[(2-methylphenoxy)methyl]phenyl]-2-oxoacetate Chemical compound COC(=O)C(=O)C1=CC=CC=C1COC1=CC=CC=C1C DVQZMPYYTUUGAK-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
- 239000000543 intermediate Substances 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 12
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 10
- 229910052794 bromium Inorganic materials 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 229910052500 inorganic mineral Inorganic materials 0.000 description 9
- 239000011707 mineral Substances 0.000 description 9
- 235000010755 mineral Nutrition 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 8
- 239000012442 inert solvent Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000003482 Pinner synthesis reaction Methods 0.000 description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 7
- 238000004817 gas chromatography Methods 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 150000002825 nitriles Chemical class 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000003701 inert diluent Substances 0.000 description 6
- 238000002955 isolation Methods 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 150000004707 phenolate Chemical class 0.000 description 6
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- OKFQSCSSXQZESR-UHFFFAOYSA-N 2-[2-[(2-methylphenoxy)methyl]phenyl]-2-oxoacetamide Chemical compound CC1=CC=CC=C1OCC1=CC=CC=C1C(=O)C(N)=O OKFQSCSSXQZESR-UHFFFAOYSA-N 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 238000003776 cleavage reaction Methods 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 5
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- GGHBSPYRYQTBDW-UHFFFAOYSA-N methyl 2-[(2-methylphenoxy)methyl]benzoate Chemical compound COC(=O)C1=CC=CC=C1COC1=CC=CC=C1C GGHBSPYRYQTBDW-UHFFFAOYSA-N 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 125000005506 phthalide group Chemical group 0.000 description 5
- 230000007017 scission Effects 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- RTVUGSBZUSWRRT-UHFFFAOYSA-N 2-[(2-methylphenoxy)methyl]benzoic acid Chemical compound CC1=CC=CC=C1OCC1=CC=CC=C1C(O)=O RTVUGSBZUSWRRT-UHFFFAOYSA-N 0.000 description 4
- CDQQUVRKDUJLIU-UHFFFAOYSA-N 2-[(2-methylphenoxy)methyl]benzoyl chloride Chemical compound CC1=CC=CC=C1OCC1=CC=CC=C1C(Cl)=O CDQQUVRKDUJLIU-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 150000001264 acyl cyanides Chemical class 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 4
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
- 150000001805 chlorine compounds Chemical class 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
- 239000003444 phase transfer catalyst Substances 0.000 description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- VGFJOKMZDHXBMU-UHFFFAOYSA-N CC=1C(=C(C(=O)O)C=CC1)COC1=C(C=CC=C1)C Chemical compound CC=1C(=C(C(=O)O)C=CC1)COC1=C(C=CC=C1)C VGFJOKMZDHXBMU-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 238000006434 Ritter amidation reaction Methods 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000417 fungicide Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 3
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 230000008707 rearrangement Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- OKVTYLOXWGCLBB-UHFFFAOYSA-N 1-bromo-2-[(2-methylphenoxy)methyl]benzene Chemical compound CC1=CC=CC=C1OCC1=CC=CC=C1Br OKVTYLOXWGCLBB-UHFFFAOYSA-N 0.000 description 2
- VLFAYAVFFCUQKR-UHFFFAOYSA-N 2-[(3,4-dimethylphenoxy)methyl]benzoyl chloride Chemical compound C1=C(C)C(C)=CC=C1OCC1=CC=CC=C1C(Cl)=O VLFAYAVFFCUQKR-UHFFFAOYSA-N 0.000 description 2
- JBLSILDRMWTCPE-UHFFFAOYSA-N 2-[(3-butylphenoxy)methyl]benzoyl chloride Chemical compound CCCCC1=CC=CC(OCC=2C(=CC=CC=2)C(Cl)=O)=C1 JBLSILDRMWTCPE-UHFFFAOYSA-N 0.000 description 2
- SJUXJYMJBZHTQL-UHFFFAOYSA-N 2-[(3-tert-butylphenoxy)methyl]benzoyl chloride Chemical compound CC(C)(C)C1=CC=CC(OCC=2C(=CC=CC=2)C(Cl)=O)=C1 SJUXJYMJBZHTQL-UHFFFAOYSA-N 0.000 description 2
- DORAAJGMBKASKI-UHFFFAOYSA-N 2-[(4-butan-2-ylphenoxy)methyl]benzoyl chloride Chemical compound C1=CC(C(C)CC)=CC=C1OCC1=CC=CC=C1C(Cl)=O DORAAJGMBKASKI-UHFFFAOYSA-N 0.000 description 2
- VJHFVGQKNWRPHO-UHFFFAOYSA-N 2-[3-methyl-2-[(2-methylphenoxy)methyl]phenyl]-2-oxoacetic acid Chemical compound Cc1ccccc1OCc1c(C)cccc1C(=O)C(O)=O VJHFVGQKNWRPHO-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- KSXDSXGUERISDJ-UHFFFAOYSA-N CC1=CC=CC(C(C(OC)=O)=O)=C1COC1=C(C)C=CC=C1 Chemical compound CC1=CC=CC(C(C(OC)=O)=O)=C1COC1=C(C)C=CC=C1 KSXDSXGUERISDJ-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 238000003747 Grignard reaction Methods 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000010306 acid treatment Methods 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000012045 crude solution Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- VMVPDELYTLSTJU-UHFFFAOYSA-N methyl 2-oxo-2-[2-(phenoxymethyl)phenyl]acetate Chemical compound COC(=O)C(=O)C1=CC=CC=C1COC1=CC=CC=C1 VMVPDELYTLSTJU-UHFFFAOYSA-N 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 125000005359 phenoxyalkyl group Chemical group 0.000 description 2
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- MNZAKDODWSQONA-UHFFFAOYSA-N 1-dibutylphosphorylbutane Chemical compound CCCCP(=O)(CCCC)CCCC MNZAKDODWSQONA-UHFFFAOYSA-N 0.000 description 1
- NOXUPQDPIYRWMN-UHFFFAOYSA-N 2-[(2,4-dichlorophenoxy)methyl]benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1COC1=CC=C(Cl)C=C1Cl NOXUPQDPIYRWMN-UHFFFAOYSA-N 0.000 description 1
- JRSYZBKNFWGHDQ-UHFFFAOYSA-N 2-[(2,4-dichlorophenoxy)methyl]benzoyl cyanide Chemical compound ClC1=CC(Cl)=CC=C1OCC1=CC=CC=C1C(=O)C#N JRSYZBKNFWGHDQ-UHFFFAOYSA-N 0.000 description 1
- QSARPTXBYCDBMG-UHFFFAOYSA-N 2-[(2,4-dimethylphenoxy)methyl]benzoyl chloride Chemical compound CC1=CC(C)=CC=C1OCC1=CC=CC=C1C(Cl)=O QSARPTXBYCDBMG-UHFFFAOYSA-N 0.000 description 1
- JFHRBHNVHJUJPZ-UHFFFAOYSA-N 2-[(2,4-dimethylphenoxy)methyl]benzoyl cyanide Chemical compound CC1=CC(C)=CC=C1OCC1=CC=CC=C1C(=O)C#N JFHRBHNVHJUJPZ-UHFFFAOYSA-N 0.000 description 1
- ZXPHQIARQDLMAF-UHFFFAOYSA-N 2-[(2-chloro-4-ethylphenoxy)methyl]benzoyl chloride Chemical compound ClC1=CC(CC)=CC=C1OCC1=CC=CC=C1C(Cl)=O ZXPHQIARQDLMAF-UHFFFAOYSA-N 0.000 description 1
- ZVNHSSAAHFMHDN-UHFFFAOYSA-N 2-[(2-chloro-4-ethylphenoxy)methyl]benzoyl cyanide Chemical compound ClC1=CC(CC)=CC=C1OCC1=CC=CC=C1C(=O)C#N ZVNHSSAAHFMHDN-UHFFFAOYSA-N 0.000 description 1
- RTYDQGNPARRJLW-UHFFFAOYSA-N 2-[(2-chloro-4-methylphenoxy)methyl]benzoyl chloride Chemical compound ClC1=CC(C)=CC=C1OCC1=CC=CC=C1C(Cl)=O RTYDQGNPARRJLW-UHFFFAOYSA-N 0.000 description 1
- WVZYOCIKKVVVBY-UHFFFAOYSA-N 2-[(2-chloro-4-methylphenoxy)methyl]benzoyl cyanide Chemical compound ClC1=CC(C)=CC=C1OCC1=CC=CC=C1C(=O)C#N WVZYOCIKKVVVBY-UHFFFAOYSA-N 0.000 description 1
- VFJRWTNTDHKEIS-UHFFFAOYSA-N 2-[(2-chlorophenoxy)methyl]benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1COC1=CC=CC=C1Cl VFJRWTNTDHKEIS-UHFFFAOYSA-N 0.000 description 1
- ABYWEWMIAZVTKZ-UHFFFAOYSA-N 2-[(2-chlorophenoxy)methyl]benzoyl cyanide Chemical compound ClC1=CC=CC=C1OCC1=CC=CC=C1C(=O)C#N ABYWEWMIAZVTKZ-UHFFFAOYSA-N 0.000 description 1
- QDDOHZYNGXEZRE-UHFFFAOYSA-N 2-[(2-ethyl-4-methylphenoxy)methyl]benzoyl chloride Chemical compound CCC1=CC(C)=CC=C1OCC1=CC=CC=C1C(Cl)=O QDDOHZYNGXEZRE-UHFFFAOYSA-N 0.000 description 1
- NSDHJBQEGGCTLC-UHFFFAOYSA-N 2-[(2-ethyl-4-methylphenoxy)methyl]benzoyl cyanide Chemical compound CCC1=CC(C)=CC=C1OCC1=CC=CC=C1C(=O)C#N NSDHJBQEGGCTLC-UHFFFAOYSA-N 0.000 description 1
- CXUVITWISULTRW-UHFFFAOYSA-N 2-[(2-ethylphenoxy)methyl]benzoyl chloride Chemical compound CCC1=CC=CC=C1OCC1=CC=CC=C1C(Cl)=O CXUVITWISULTRW-UHFFFAOYSA-N 0.000 description 1
- ZSAOWQTVJRDKRU-UHFFFAOYSA-N 2-[(2-ethylphenoxy)methyl]benzoyl cyanide Chemical compound CCC1=CC=CC=C1OCC1=CC=CC=C1C(=O)C#N ZSAOWQTVJRDKRU-UHFFFAOYSA-N 0.000 description 1
- YWDSPGIOOMMQJU-UHFFFAOYSA-N 2-[(2-fluorophenoxy)methyl]benzoyl chloride Chemical compound FC1=CC=CC=C1OCC1=CC=CC=C1C(Cl)=O YWDSPGIOOMMQJU-UHFFFAOYSA-N 0.000 description 1
- SSWUSLNAHVPHIY-UHFFFAOYSA-N 2-[(2-fluorophenoxy)methyl]benzoyl cyanide Chemical compound FC1=CC=CC=C1OCC1=CC=CC=C1C(=O)C#N SSWUSLNAHVPHIY-UHFFFAOYSA-N 0.000 description 1
- QTJWQKKAKRKRTJ-UHFFFAOYSA-N 2-[(2-methyl-4-sulfophenoxy)methyl]benzoic acid Chemical compound CC1=CC(S(O)(=O)=O)=CC=C1OCC1=CC=CC=C1C(O)=O QTJWQKKAKRKRTJ-UHFFFAOYSA-N 0.000 description 1
- HPHBRIBCLYDUPQ-UHFFFAOYSA-N 2-[(3-chlorophenoxy)methyl]benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1COC1=CC=CC(Cl)=C1 HPHBRIBCLYDUPQ-UHFFFAOYSA-N 0.000 description 1
- KUQLDSFRKMBMHH-UHFFFAOYSA-N 2-[(3-chlorophenoxy)methyl]benzoyl cyanide Chemical compound ClC1=CC=CC(OCC=2C(=CC=CC=2)C(=O)C#N)=C1 KUQLDSFRKMBMHH-UHFFFAOYSA-N 0.000 description 1
- RIFLNJXQZJNFSZ-UHFFFAOYSA-N 2-[(3-ethylphenoxy)methyl]benzoyl chloride Chemical compound CCC1=CC=CC(OCC=2C(=CC=CC=2)C(Cl)=O)=C1 RIFLNJXQZJNFSZ-UHFFFAOYSA-N 0.000 description 1
- LFAIXYVIEQIMQM-UHFFFAOYSA-N 2-[(3-ethylphenoxy)methyl]benzoyl cyanide Chemical compound CCC1=CC=CC(OCC=2C(=CC=CC=2)C(=O)C#N)=C1 LFAIXYVIEQIMQM-UHFFFAOYSA-N 0.000 description 1
- PJSGSXPTLKTGEW-UHFFFAOYSA-N 2-[(3-fluorophenoxy)methyl]benzoyl chloride Chemical compound FC1=CC=CC(OCC=2C(=CC=CC=2)C(Cl)=O)=C1 PJSGSXPTLKTGEW-UHFFFAOYSA-N 0.000 description 1
- GGXNKOBRLBFFRE-UHFFFAOYSA-N 2-[(3-fluorophenoxy)methyl]benzoyl cyanide Chemical compound FC1=CC=CC(OCC=2C(=CC=CC=2)C(=O)C#N)=C1 GGXNKOBRLBFFRE-UHFFFAOYSA-N 0.000 description 1
- BVVXHCSTIGHDHP-UHFFFAOYSA-N 2-[(3-methylphenoxy)methyl]benzoyl chloride Chemical compound CC1=CC=CC(OCC=2C(=CC=CC=2)C(Cl)=O)=C1 BVVXHCSTIGHDHP-UHFFFAOYSA-N 0.000 description 1
- ZLKUDWZKDDLNRP-UHFFFAOYSA-N 2-[(3-methylphenoxy)methyl]benzoyl cyanide Chemical compound CC1=CC=CC(OCC=2C(=CC=CC=2)C(=O)C#N)=C1 ZLKUDWZKDDLNRP-UHFFFAOYSA-N 0.000 description 1
- IDFNXYWLEXIJHW-UHFFFAOYSA-N 2-[(4-chloro-2-ethylphenoxy)methyl]benzoyl chloride Chemical compound CCC1=CC(Cl)=CC=C1OCC1=CC=CC=C1C(Cl)=O IDFNXYWLEXIJHW-UHFFFAOYSA-N 0.000 description 1
- MOQICVYUGBEGFT-UHFFFAOYSA-N 2-[(4-chloro-2-ethylphenoxy)methyl]benzoyl cyanide Chemical compound CCC1=CC(Cl)=CC=C1OCC1=CC=CC=C1C(=O)C#N MOQICVYUGBEGFT-UHFFFAOYSA-N 0.000 description 1
- VFNWPLSMUFRCQV-UHFFFAOYSA-N 2-[(4-chloro-2-methylphenoxy)methyl]benzoyl chloride Chemical compound CC1=CC(Cl)=CC=C1OCC1=CC=CC=C1C(Cl)=O VFNWPLSMUFRCQV-UHFFFAOYSA-N 0.000 description 1
- ASJPQPAFKDMEBI-UHFFFAOYSA-N 2-[(4-chloro-2-methylphenoxy)methyl]benzoyl cyanide Chemical compound CC1=CC(Cl)=CC=C1OCC1=CC=CC=C1C(=O)C#N ASJPQPAFKDMEBI-UHFFFAOYSA-N 0.000 description 1
- MHBHZPVPLUNFLP-UHFFFAOYSA-N 2-[(4-chlorophenoxy)methyl]benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1COC1=CC=C(Cl)C=C1 MHBHZPVPLUNFLP-UHFFFAOYSA-N 0.000 description 1
- DNZLBWFELMFRBW-UHFFFAOYSA-N 2-[(4-chlorophenoxy)methyl]benzoyl cyanide Chemical compound C1=CC(Cl)=CC=C1OCC1=CC=CC=C1C(=O)C#N DNZLBWFELMFRBW-UHFFFAOYSA-N 0.000 description 1
- PTIIHSGQNFCWQG-UHFFFAOYSA-N 2-[(4-ethyl-2-methylphenoxy)methyl]benzoyl chloride Chemical compound CC1=CC(CC)=CC=C1OCC1=CC=CC=C1C(Cl)=O PTIIHSGQNFCWQG-UHFFFAOYSA-N 0.000 description 1
- BXQXKLKUYCPLDG-UHFFFAOYSA-N 2-[(4-ethyl-2-methylphenoxy)methyl]benzoyl cyanide Chemical compound CC1=CC(CC)=CC=C1OCC1=CC=CC=C1C(=O)C#N BXQXKLKUYCPLDG-UHFFFAOYSA-N 0.000 description 1
- HTQJGOMGRMMZFM-UHFFFAOYSA-N 2-[(4-ethylphenoxy)methyl]-4-methoxybenzoyl chloride Chemical compound C1=CC(CC)=CC=C1OCC1=CC(OC)=CC=C1C(Cl)=O HTQJGOMGRMMZFM-UHFFFAOYSA-N 0.000 description 1
- NZYZYGGFZWTYCZ-UHFFFAOYSA-N 2-[(4-ethylphenoxy)methyl]benzoyl chloride Chemical compound C1=CC(CC)=CC=C1OCC1=CC=CC=C1C(Cl)=O NZYZYGGFZWTYCZ-UHFFFAOYSA-N 0.000 description 1
- HVXGMXIHHRHDJK-UHFFFAOYSA-N 2-[(4-ethylphenoxy)methyl]benzoyl cyanide Chemical compound C1=CC(CC)=CC=C1OCC1=CC=CC=C1C(=O)C#N HVXGMXIHHRHDJK-UHFFFAOYSA-N 0.000 description 1
- IDWIJALDPKZWCE-UHFFFAOYSA-N 2-[(4-fluoro-2-methylphenoxy)methyl]benzoyl chloride Chemical compound CC1=CC(F)=CC=C1OCC1=CC=CC=C1C(Cl)=O IDWIJALDPKZWCE-UHFFFAOYSA-N 0.000 description 1
- RGADSQRGWHOEFR-UHFFFAOYSA-N 2-[(4-fluoro-2-methylphenoxy)methyl]benzoyl cyanide Chemical compound CC1=CC(F)=CC=C1OCC1=CC=CC=C1C(=O)C#N RGADSQRGWHOEFR-UHFFFAOYSA-N 0.000 description 1
- QYGXWLDWTVXKMK-UHFFFAOYSA-N 2-[(4-fluorophenoxy)methyl]benzoyl chloride Chemical compound C1=CC(F)=CC=C1OCC1=CC=CC=C1C(Cl)=O QYGXWLDWTVXKMK-UHFFFAOYSA-N 0.000 description 1
- COUKVVYFXGVCDP-UHFFFAOYSA-N 2-[(4-fluorophenoxy)methyl]benzoyl cyanide Chemical compound C1=CC(F)=CC=C1OCC1=CC=CC=C1C(=O)C#N COUKVVYFXGVCDP-UHFFFAOYSA-N 0.000 description 1
- HJUYBUJYQVZMRJ-UHFFFAOYSA-N 2-[(4-methylphenoxy)methyl]benzoyl chloride Chemical compound C1=CC(C)=CC=C1OCC1=CC=CC=C1C(Cl)=O HJUYBUJYQVZMRJ-UHFFFAOYSA-N 0.000 description 1
- TWHDROQJJXLQGK-UHFFFAOYSA-N 2-[(4-methylphenoxy)methyl]benzoyl cyanide Chemical compound C1=CC(C)=CC=C1OCC1=CC=CC=C1C(=O)C#N TWHDROQJJXLQGK-UHFFFAOYSA-N 0.000 description 1
- WOFHVEMOCUISEK-UHFFFAOYSA-N 2-[[2-(trifluoromethyl)phenoxy]methyl]benzoyl chloride Chemical compound FC(F)(F)C1=CC=CC=C1OCC1=CC=CC=C1C(Cl)=O WOFHVEMOCUISEK-UHFFFAOYSA-N 0.000 description 1
- GASNLXIOOUOQTA-UHFFFAOYSA-N 2-[[2-(trifluoromethyl)phenoxy]methyl]benzoyl cyanide Chemical compound FC(F)(F)C1=CC=CC=C1OCC1=CC=CC=C1C(=O)C#N GASNLXIOOUOQTA-UHFFFAOYSA-N 0.000 description 1
- MHCAKXYZWFNGEL-UHFFFAOYSA-N 2-[[3-(trifluoromethyl)phenoxy]methyl]benzoyl cyanide Chemical compound FC(F)(F)C1=CC=CC(OCC=2C(=CC=CC=2)C(=O)C#N)=C1 MHCAKXYZWFNGEL-UHFFFAOYSA-N 0.000 description 1
- YMJYJOVXHURNFS-UHFFFAOYSA-N 2-[[4-(trifluoromethyl)phenoxy]methyl]benzoyl chloride Chemical compound C1=CC(C(F)(F)F)=CC=C1OCC1=CC=CC=C1C(Cl)=O YMJYJOVXHURNFS-UHFFFAOYSA-N 0.000 description 1
- JJAFKARCDXBYPM-UHFFFAOYSA-N 2-[[4-(trifluoromethyl)phenoxy]methyl]benzoyl cyanide Chemical compound C1=CC(C(F)(F)F)=CC=C1OCC1=CC=CC=C1C(=O)C#N JJAFKARCDXBYPM-UHFFFAOYSA-N 0.000 description 1
- WFRSBFQCMFWRTD-UHFFFAOYSA-N 2-oxo-2-phenylacetamide Chemical compound NC(=O)C(=O)C1=CC=CC=C1 WFRSBFQCMFWRTD-UHFFFAOYSA-N 0.000 description 1
- ILYSAKHOYBPSPC-UHFFFAOYSA-N 2-phenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1 ILYSAKHOYBPSPC-UHFFFAOYSA-N 0.000 description 1
- MPJOJCZVGBOVOV-UHFFFAOYSA-N 2-phenylbenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C1=CC=CC=C1 MPJOJCZVGBOVOV-UHFFFAOYSA-N 0.000 description 1
- NGDMTUROPZMJBA-UHFFFAOYSA-N 2-phenylbenzoyl cyanide Chemical compound N#CC(=O)C1=CC=CC=C1C1=CC=CC=C1 NGDMTUROPZMJBA-UHFFFAOYSA-N 0.000 description 1
- QRQXBVDDGHHWCA-UHFFFAOYSA-N 3-methyl-3-(2-methylbut-3-en-2-yloxy)but-1-ene Chemical compound C=CC(C)(C)OC(C)(C)C=C QRQXBVDDGHHWCA-UHFFFAOYSA-N 0.000 description 1
- RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 206010029897 Obsessive thoughts Diseases 0.000 description 1
- 238000006956 Pummerer reaction Methods 0.000 description 1
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- UNLSXXHOHZUADN-UHFFFAOYSA-N barium cyanide Chemical compound [Ba+2].N#[C-].N#[C-] UNLSXXHOHZUADN-UHFFFAOYSA-N 0.000 description 1
- STCCCZWPJPHQDO-UHFFFAOYSA-M benzyl(tributyl)phosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CC1=CC=CC=C1 STCCCZWPJPHQDO-UHFFFAOYSA-M 0.000 description 1
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- YGPAXTKKXYABEL-UHFFFAOYSA-M benzyl(triphenyl)azanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[N+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 YGPAXTKKXYABEL-UHFFFAOYSA-M 0.000 description 1
- 125000006515 benzyloxy alkyl group Chemical group 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 125000006226 butoxyethyl group Chemical group 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- LEKPFOXEZRZPGW-UHFFFAOYSA-N copper;dicyanide Chemical compound [Cu+2].N#[C-].N#[C-] LEKPFOXEZRZPGW-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical class OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910001867 inorganic solvent Inorganic materials 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- FQGYCXFLEQVDJQ-UHFFFAOYSA-N mercury dicyanide Chemical compound N#C[Hg]C#N FQGYCXFLEQVDJQ-UHFFFAOYSA-N 0.000 description 1
- 238000006140 methanolysis reaction Methods 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- NNHDCYABCHZSQT-FBMGVBCBSA-N methyl (2e)-2-hydroxyimino-2-[2-[(2-methylphenoxy)methyl]phenyl]acetate Chemical compound COC(=O)C(=N\O)\C1=CC=CC=C1COC1=CC=CC=C1C NNHDCYABCHZSQT-FBMGVBCBSA-N 0.000 description 1
- XNHZFKFMBWLXGT-UHFFFAOYSA-N methyl 2-[(4-tert-butyl-2-methylphenoxy)methyl]benzoate Chemical compound COC(=O)C1=CC=CC=C1COC1=CC=C(C(C)(C)C)C=C1C XNHZFKFMBWLXGT-UHFFFAOYSA-N 0.000 description 1
- SZAFHPVKHPLRRD-UHFFFAOYSA-N methyl 2-naphthalen-1-yl-2-oxoacetate Chemical compound C1=CC=C2C(C(=O)C(=O)OC)=CC=CC2=C1 SZAFHPVKHPLRRD-UHFFFAOYSA-N 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- IRMVRAABQYONJL-UHFFFAOYSA-N morpholin-4-yl formate Chemical compound O=CON1CCOCC1 IRMVRAABQYONJL-UHFFFAOYSA-N 0.000 description 1
- NTYICSDTCGMBQM-UHFFFAOYSA-N n,n-bis(2-methylpropyl)formamide Chemical compound CC(C)CN(C=O)CC(C)C NTYICSDTCGMBQM-UHFFFAOYSA-N 0.000 description 1
- XRPITCBWOUOJTH-UHFFFAOYSA-N n,n-diethylpyridin-2-amine Chemical compound CCN(CC)C1=CC=CC=N1 XRPITCBWOUOJTH-UHFFFAOYSA-N 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- XRAJPBGAOXEAAB-UHFFFAOYSA-N n-tert-butyl-2-[2-[(2-methylphenoxy)methyl]phenyl]-2-oxoacetamide Chemical compound CC1=CC=CC=C1OCC1=CC=CC=C1C(=O)C(=O)NC(C)(C)C XRAJPBGAOXEAAB-UHFFFAOYSA-N 0.000 description 1
- SVWOSRJNHDBRGF-UHFFFAOYSA-N n-tert-butyl-2-oxo-2-phenylacetamide Chemical compound CC(C)(C)NC(=O)C(=O)C1=CC=CC=C1 SVWOSRJNHDBRGF-UHFFFAOYSA-N 0.000 description 1
- NSNPSJGHTQIXDO-UHFFFAOYSA-N naphthalene-1-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)=CC=CC2=C1 NSNPSJGHTQIXDO-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- ATYBXHSAIOKLMG-UHFFFAOYSA-N oxepin Chemical compound O1C=CC=CC=C1 ATYBXHSAIOKLMG-UHFFFAOYSA-N 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000006103 sulfonylation Effects 0.000 description 1
- 238000005694 sulfonylation reaction Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical class CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- DXJLCRNXYNRGRA-UHFFFAOYSA-M tributyl(methyl)azanium;iodide Chemical compound [I-].CCCC[N+](C)(CCCC)CCCC DXJLCRNXYNRGRA-UHFFFAOYSA-M 0.000 description 1
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/08—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reaction of hydroxylamines with carbonyl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/14—Preparation of carboxylic acid nitriles by reaction of cyanides with halogen-containing compounds with replacement of halogen atoms by cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/17—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and doubly-bound oxygen atoms bound to the same acyclic carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Toxicology (AREA)
- Health & Medical Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4042280A DE4042280A1 (de) | 1990-12-31 | 1990-12-31 | Verfahren zur herstellung von (alpha)-ketocarbonsaeureestern |
| DE4042273A DE4042273A1 (de) | 1990-12-31 | 1990-12-31 | Verfahren zur herstellung von (alpha)-ketocarbonsaeureestern |
| DE4042283A DE4042283A1 (de) | 1990-12-31 | 1990-12-31 | Verfahren zur herstellung von 2-phenoxymethylbenzoesaeuren |
| DE4042282A DE4042282A1 (de) | 1990-12-31 | 1990-12-31 | O-substituierte benzoylcyanide |
| DE4042272A DE4042272A1 (de) | 1990-12-31 | 1990-12-31 | Verfahren zur herstellung von e-oximethern von phenylglyoxylsaeureestern |
| DE4042271A DE4042271A1 (de) | 1990-12-31 | 1990-12-31 | Verfahren zur herstellung von arylglyoxylsaeureestern |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HU914162D0 HU914162D0 (en) | 1992-03-30 |
| HUT61264A HUT61264A (en) | 1992-12-28 |
| HU209283B true HU209283B (en) | 1994-04-28 |
Family
ID=27544603
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU914162A HU209283B (en) | 1990-12-31 | 1991-12-30 | Process for producing e-oxime ethers of phenylglyoxylic acid esters |
Country Status (13)
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5258551A (en) * | 1991-12-18 | 1993-11-02 | Shionogi & Co., Ltd. | Process for producing α-ketoamide derivative |
| DE4203170A1 (de) | 1992-02-05 | 1993-08-12 | Basf Ag | Verfahren zur herstellung von e-oximethern von phenylglyoxylsaeureestern |
| DE4311722C1 (de) * | 1993-04-08 | 1994-04-07 | Basf Ag | Verfahren zur Herstellung von Halogenmethyl-benzoylcyaniden und neue Halogenmethyl-benzoylcyanide |
| DE4320499A1 (de) * | 1993-05-14 | 1994-11-17 | Bayer Ag | Verfahren zur Herstellung von 2-Oximinoessigsäurederivaten |
| DK0658541T3 (da) * | 1993-07-02 | 1998-10-19 | Shionogi & Co | Fremgangsmåde til fremstilling af carboxylsyrederivat |
| JP4114948B2 (ja) * | 1994-06-10 | 2008-07-09 | バイエル、クロップ、サイエンス、アクチェンゲゼルシャフト | α−メトキシイミノカルボン酸メチルアミドの製造方法およびその中間生成物 |
| UA49813C2 (uk) * | 1994-11-24 | 2002-10-15 | Басф Акцієнгезельшафт | Спосіб одержання галогенметилбензоїлціанідів |
| DE4442560A1 (de) * | 1994-11-30 | 1996-06-05 | Basf Ag | Iminooxybenzylcrotonsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19648009A1 (de) | 1996-11-20 | 1998-05-28 | Bayer Ag | Glyoxylsäureamide |
| AU5463398A (en) * | 1996-11-26 | 1998-06-22 | E.I. Du Pont De Nemours And Company | Methyl substituted fungicides and arthropodicides |
| DE19726201A1 (de) | 1997-06-20 | 1998-12-24 | Bayer Ag | Glyoxylsäureamide |
| DE19848200A1 (de) * | 1998-10-20 | 2000-04-27 | Basf Ag | Verfahren zur Trocknung von Phenoxymethylbenzoesäuren |
| DE19958165A1 (de) | 1999-12-02 | 2001-06-07 | Bayer Ag | Glyoxylsäureamide |
| US7238835B2 (en) * | 2003-12-22 | 2007-07-03 | Sanofi-Aventis Deutschland Gmbh | Process for the preparation of substituted 2-(phenoxymethyl) benzoic acids |
| US20070054948A1 (en) * | 2004-09-02 | 2007-03-08 | Lilach Hedvati | Purification of olmesartan medoxomil |
| KR20090102883A (ko) * | 2004-09-02 | 2009-09-30 | 테바 파마슈티컬 인더스트리즈 리미티드 | 올메살탄 메독소밀의 정제 |
| CN100443463C (zh) * | 2005-06-28 | 2008-12-17 | 沈阳化工研究院 | 取代的对三氟甲基苯醚类化合物及其制备与应用 |
| JP5417860B2 (ja) * | 2008-08-26 | 2014-02-19 | 住友化学株式会社 | α−ヒドロキシエステル類の製造方法 |
| JP2012516868A (ja) | 2009-02-05 | 2012-07-26 | ビーエーエスエフ ソシエタス・ヨーロピア | ２−ハロゲノメチルフェニル酢酸誘導体の製造方法 |
| CN101664031B (zh) * | 2009-09-30 | 2012-09-05 | 南宁市德丰富化工有限责任公司 | 一种含醚菌酯和春雷霉素的杀菌组合物 |
| CN102391121B (zh) * | 2011-08-04 | 2014-06-18 | 京博农化科技股份有限公司 | 2-（2-甲基苯氧基）-亚甲基苯基乙醛酸甲酯的制备方法 |
| WO2013144924A1 (en) | 2012-03-29 | 2013-10-03 | Rallis India Ltd. | An improved process for the synthesis of strobilurin fungicides viz trifloxystrobin and kresoxim-methyl |
| CN103787916B (zh) * | 2014-01-15 | 2016-07-13 | 京博农化科技股份有限公司 | 一种肟菌酯的制备方法 |
| CN104529818A (zh) * | 2014-12-16 | 2015-04-22 | 江苏耕耘化学有限公司 | 制备(e)-2-(2-取代苯基)-2-甲氧亚胺基乙酸衍生物的方法 |
| CN105884651B (zh) * | 2016-04-25 | 2019-04-12 | 山东理工大学 | 一种醚菌酯中间体的制备装置及方法 |
| CN109651190A (zh) * | 2018-12-28 | 2019-04-19 | 京博农化科技有限公司 | 一种醚菌酯的合成方法 |
| CN113754527B (zh) * | 2021-09-07 | 2024-01-12 | 山东京博农化科技股份有限公司 | 一种醚菌酯中间体的合成方法 |
| CN114478241A (zh) * | 2021-12-31 | 2022-05-13 | 山东京博生物科技有限公司 | 一种芳甲酰基甲酸酯的制备方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1279682B (de) * | 1961-08-12 | 1968-10-10 | Boehringer & Soehne Gmbh | Verfahren zur Herstellung von 6, 11-Dihydro-dibenzo-[b, e]-oxepin- bzw. -thiepin-11-on |
| DE2365755A1 (de) * | 1972-09-12 | 1976-04-08 | Sagami Chem Res | Alpha-ketosaeurederivate und verfahren zu ihrer herstellung |
| DE2528211C3 (de) * | 1975-06-25 | 1980-03-06 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Acylcyaniden |
| DE2708189C2 (de) | 1977-02-25 | 1985-07-04 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Phenylglyoxylsäureestern |
| US4234739A (en) | 1978-12-05 | 1980-11-18 | Stauffer Chemical Company | Method for preparing glyoxylic acids and derivatives thereof |
| DE3002203A1 (de) | 1980-01-22 | 1981-07-23 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von (alpha)-ketocarbonsaeure-n-tert.-butylamiden |
| DE3009044A1 (de) | 1980-03-08 | 1981-09-24 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von (alpha)-ketocarbon-n-acylamiden |
| DE3623921A1 (de) * | 1986-07-16 | 1988-01-21 | Basf Ag | Oximether und diese enthaltende fungizide |
| GB8617648D0 (en) | 1986-07-18 | 1986-08-28 | Ici Plc | Fungicides |
| DE3705389A1 (de) | 1987-02-20 | 1988-09-01 | Basf Ag | Substituierte crotonsaeureester und diese enthaltende fungizide |
| ES2093013T3 (es) * | 1989-05-17 | 1996-12-16 | Shionogi & Co | Derivados de alcoxiiminoacetamida y su aplicacion como fungicidas. |
| FR2647110B1 (fr) * | 1989-05-19 | 1991-07-26 | Atochem | Procede de synthese de cyanures d'acyle |
| FR2647109B1 (fr) * | 1989-05-19 | 1991-07-26 | Atochem | Procede de preparation de cyanures d'acyle en milieu anhydre |
| JPH02306934A (ja) * | 1989-05-19 | 1990-12-20 | Mitsubishi Petrochem Co Ltd | ４―（アルキルフェノキシ）酪酸の製造方法 |
| DE3917352A1 (de) * | 1989-05-27 | 1990-11-29 | Basf Ag | Neue oximether und diese enthaltende fungizide |
-
1991
- 1991-12-10 DK DK91121148.0T patent/DK0493711T3/da active
- 1991-12-10 DK DK96101025.3T patent/DK0712835T3/da active
- 1991-12-10 EP EP96101039A patent/EP0718279B1/de not_active Expired - Lifetime
- 1991-12-10 EP EP96101038A patent/EP0712833B1/de not_active Expired - Lifetime
- 1991-12-10 AT AT96101025T patent/ATE157079T1/de not_active IP Right Cessation
- 1991-12-10 ES ES96101039T patent/ES2107923T3/es not_active Expired - Lifetime
- 1991-12-10 AT AT91121148T patent/ATE143356T1/de not_active IP Right Cessation
- 1991-12-10 ES ES96101038T patent/ES2105904T3/es not_active Expired - Lifetime
- 1991-12-10 AT AT96101039T patent/ATE158569T1/de not_active IP Right Cessation
- 1991-12-10 EP EP91121148A patent/EP0493711B1/de not_active Expired - Lifetime
- 1991-12-10 DE DE59108229T patent/DE59108229D1/de not_active Expired - Lifetime
- 1991-12-10 AT AT96101038T patent/ATE157643T1/de not_active IP Right Cessation
- 1991-12-10 DK DK96101038.6T patent/DK0712833T3/da active
- 1991-12-10 EP EP96101025A patent/EP0712835B1/de not_active Expired - Lifetime
- 1991-12-10 ES ES96101025T patent/ES2105903T3/es not_active Expired - Lifetime
- 1991-12-10 ES ES91121148T patent/ES2091278T3/es not_active Expired - Lifetime
- 1991-12-10 DE DE59108848T patent/DE59108848D1/de not_active Expired - Lifetime
- 1991-12-10 DE DE59108861T patent/DE59108861D1/de not_active Expired - Lifetime
- 1991-12-10 DK DK96101039.4T patent/DK0718279T3/da active
- 1991-12-10 DE DE59108832T patent/DE59108832D1/de not_active Expired - Lifetime
- 1991-12-13 US US07/806,295 patent/US5221762A/en not_active Expired - Lifetime
- 1991-12-16 IL IL116442A patent/IL116442A/xx not_active IP Right Cessation
- 1991-12-16 IL IL100387A patent/IL100387A/xx not_active IP Right Cessation
- 1991-12-16 IL IL116443A patent/IL116443A/xx not_active IP Right Cessation
- 1991-12-20 JP JP33812791A patent/JP3343263B2/ja not_active Expired - Fee Related
- 1991-12-24 AU AU90082/91A patent/AU641579B2/en not_active Expired
- 1991-12-30 KR KR1019910025541A patent/KR100214191B1/ko not_active Expired - Lifetime
- 1991-12-30 CA CA002058553A patent/CA2058553C/en not_active Expired - Lifetime
- 1991-12-30 CA CA002367876A patent/CA2367876C/en not_active Expired - Lifetime
- 1991-12-30 HU HU914162A patent/HU209283B/hu unknown
-
1995
- 1995-12-19 IL IL11644295A patent/IL116442A0/xx unknown
- 1995-12-19 IL IL11644395A patent/IL116443A0/xx unknown
-
1996
- 1996-10-09 GR GR960402642T patent/GR3021280T3/el unknown
-
1997
- 1997-08-22 GR GR970402161T patent/GR3024518T3/el unknown
- 1997-10-29 GR GR970402856T patent/GR3025219T3/el unknown
- 1997-11-12 GR GR970403012T patent/GR3025370T3/el unknown
-
2000
- 2000-04-03 JP JP2000100964A patent/JP3378555B2/ja not_active Expired - Fee Related
-
2002
- 2002-04-18 JP JP2002116019A patent/JP3378576B2/ja not_active Expired - Fee Related
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HU209283B (en) | Process for producing e-oxime ethers of phenylglyoxylic acid esters | |
| KR100314118B1 (ko) | N-페닐아세트아미노니트릴 | |
| JP5350790B2 (ja) | マンジプロパミドとその誘導体の合成方法 | |
| EP0605392A1 (en) | Process for producing methoxyminoacetamide compounds | |
| US7169955B2 (en) | Perfluoroisopropylbenzene derivative | |
| EP0904268B1 (de) | Verfahren zur herstellung von 3-(1-hydroxyphenyl-1-alkoximinomethyl)dioxazinen | |
| KR100522712B1 (ko) | 3-(1-하이드록시페닐-1-알콕스이미노메틸)디옥사진의제조방법 | |
| HU212910B (en) | Process for preparation of n-acylated-p-amino-phenoles | |
| HU215116B (hu) | Eljárás hidroxil-amin-éterek és sóik előállítására és intermedierjeik | |
| FR2701259A1 (fr) | Procédé pour la préparation de dérivés phénylbenzamides fongicides agricoles. | |
| KR100530600B1 (ko) | 3-(1-하이드록시페닐-1-알콕스이미노메틸)디옥사진의제조방법 | |
| Wolf et al. | 11) Patent Number: 45 Date of Patent | |
| KR100470382B1 (ko) | 3-(1-하이드록시페닐-1-알콕스이미노메틸)디옥사진의제조방법 | |
| JP2660330B2 (ja) | チオフェン誘導体及びその製造方法 | |
| DE4042280A1 (de) | Verfahren zur herstellung von (alpha)-ketocarbonsaeureestern | |
| CA2577942A1 (en) | Chiral 3-halophthalic acid derivatives | |
| KR20020051926A (ko) | 2-(2-하이드록시페닐)-2-(알콕시이미노)-ｎ-메틸아세트아미드 유도체의 제조방법 | |
| JPH06329609A (ja) | ２−オキシミノ酢酸誘導体の製造法 | |
| PT823890E (pt) | Processo e produtos intermedios para a preparacao de isomeros essencialmente puros esteres metilicos de acido e-2-(2-ariloximetilenofenil)-crotonicos | |
| HUP0001575A2 (hu) | Eljárások 3-(1-/2-hidroxi-fenil/-1-/alkoxi-imino/-metil)-dioxazin-származékok és intermedierjeik előállítására és az új intermedierek |