HU182885B - Process for preparing phenoxy-alkene derivatives - Google Patents
Process for preparing phenoxy-alkene derivatives Download PDFInfo
- Publication number
- HU182885B HU182885B HU79IA861A HUIA000861A HU182885B HU 182885 B HU182885 B HU 182885B HU 79IA861 A HU79IA861 A HU 79IA861A HU IA000861 A HUIA000861 A HU IA000861A HU 182885 B HU182885 B HU 182885B
- Authority
- HU
- Hungary
- Prior art keywords
- phenoxy
- group
- formula
- compound
- phenol
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 carboxy, hydroxymethyl Chemical group 0.000 claims abstract description 73
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 14
- 150000002367 halogens Chemical class 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
- 150000004714 phosphonium salts Chemical class 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 239000007858 starting material Substances 0.000 claims description 11
- 150000002989 phenols Chemical class 0.000 claims description 10
- 239000002798 polar solvent Substances 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 17
- 150000003839 salts Chemical class 0.000 abstract description 17
- QTNZUCWMRAIYCB-UHFFFAOYSA-M tributyl(ethyl)azanium;bromide Chemical compound [Br-].CCCC[N+](CC)(CCCC)CCCC QTNZUCWMRAIYCB-UHFFFAOYSA-M 0.000 abstract description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 4
- 150000005621 tetraalkylammonium salts Chemical class 0.000 abstract description 4
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 abstract description 3
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 25
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
- FJFSSESWAFPCSU-UHFFFAOYSA-N 4-[4-(trifluoromethyl)phenoxy]phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 FJFSSESWAFPCSU-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000001339 alkali metal compounds Chemical class 0.000 description 6
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- NEHGWVYDSJWTJK-UHFFFAOYSA-N ethyl 4-[4-[4-(trifluoromethyl)phenoxy]phenoxy]pent-2-enoate Chemical compound C1=CC(OC(C)C=CC(=O)OCC)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 NEHGWVYDSJWTJK-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000012433 hydrogen halide Substances 0.000 description 4
- 229910000039 hydrogen halide Inorganic materials 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000012454 non-polar solvent Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- XUCYZDCRSFGQOP-UHFFFAOYSA-N 3,4-dibromopentanoic acid Chemical compound CC(Br)C(Br)CC(O)=O XUCYZDCRSFGQOP-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000006266 etherification reaction Methods 0.000 description 3
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- YIYBQIKDCADOSF-UHFFFAOYSA-N pentenoic acid group Chemical group C(C=CCC)(=O)O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- XKBVEHVQDYRJCW-UHFFFAOYSA-N 4-[2-chloro-4-(trifluoromethyl)phenoxy]phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(C(F)(F)F)C=C1Cl XKBVEHVQDYRJCW-UHFFFAOYSA-N 0.000 description 2
- ZJXKMHFMOPXCOJ-UHFFFAOYSA-N 4-[4-[4-(trifluoromethyl)phenoxy]phenoxy]pent-2-enoic acid Chemical compound C1=CC(OC(C)C=CC(O)=O)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 ZJXKMHFMOPXCOJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 0.000 description 2
- GEHMWSIEKHOKJZ-UHFFFAOYSA-M benzyl(trioctyl)azanium;chloride Chemical compound [Cl-].CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CC1=CC=CC=C1 GEHMWSIEKHOKJZ-UHFFFAOYSA-M 0.000 description 2
- USFRYJRPHFMVBZ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 USFRYJRPHFMVBZ-UHFFFAOYSA-M 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 2
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- SYZCZDCAEVUSPM-UHFFFAOYSA-M tetrahexylazanium;bromide Chemical compound [Br-].CCCCCC[N+](CCCCCC)(CCCCCC)CCCCCC SYZCZDCAEVUSPM-UHFFFAOYSA-M 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 238000012795 verification Methods 0.000 description 2
- XLHUBROMZOAQMV-UHFFFAOYSA-N 1,4-benzosemiquinone Chemical group [O]C1=CC=C(O)C=C1 XLHUBROMZOAQMV-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- LQUKCFROPMVLKN-UHFFFAOYSA-N 2-[4-(trifluoromethyl)phenoxy]phenol Chemical compound OC1=CC=CC=C1OC1=CC=C(C(F)(F)F)C=C1 LQUKCFROPMVLKN-UHFFFAOYSA-N 0.000 description 1
- NIONDZDPPYHYKY-UHFFFAOYSA-N 2-hexenoic acid Chemical compound CCCC=CC(O)=O NIONDZDPPYHYKY-UHFFFAOYSA-N 0.000 description 1
- WPGHPGAUFIJVJF-UHFFFAOYSA-N 3,5-dichloropyridine Chemical compound ClC1=CN=CC(Cl)=C1 WPGHPGAUFIJVJF-UHFFFAOYSA-N 0.000 description 1
- AJIHBUNFLVGSRK-UHFFFAOYSA-N 4-(4-bromo-2-chlorophenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(Br)C=C1Cl AJIHBUNFLVGSRK-UHFFFAOYSA-N 0.000 description 1
- HMBBTPMHPQGJMR-UHFFFAOYSA-N 4-(4-bromophenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(Br)C=C1 HMBBTPMHPQGJMR-UHFFFAOYSA-N 0.000 description 1
- XQMRZWSYBUCVAX-UHFFFAOYSA-N 4-(4-chlorophenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(Cl)C=C1 XQMRZWSYBUCVAX-UHFFFAOYSA-N 0.000 description 1
- SDGFJYRTWKBZFB-UHFFFAOYSA-N 4-(4-methylphenoxy)phenol Chemical compound C1=CC(C)=CC=C1OC1=CC=C(O)C=C1 SDGFJYRTWKBZFB-UHFFFAOYSA-N 0.000 description 1
- DCCDSAOUQRQDEL-UHFFFAOYSA-N 4-(4-nitrophenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C([N+]([O-])=O)C=C1 DCCDSAOUQRQDEL-UHFFFAOYSA-N 0.000 description 1
- PAVKZCYKRPHZIQ-UHFFFAOYSA-N 4-[2-(trifluoromethyl)phenoxy]phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC=C1C(F)(F)F PAVKZCYKRPHZIQ-UHFFFAOYSA-N 0.000 description 1
- IWLRGEKAYJALDI-UHFFFAOYSA-N 4-[2-nitro-4-(trifluoromethyl)phenoxy]phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O IWLRGEKAYJALDI-UHFFFAOYSA-N 0.000 description 1
- QBUZGHPDFUNKIZ-UHFFFAOYSA-N 4-[3-(trifluoromethyl)phenoxy]phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC(C(F)(F)F)=C1 QBUZGHPDFUNKIZ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- YBWAKIKBIOTBEA-UHFFFAOYSA-N ClC1=CC=C(OC2=CC=C(OC(C=CC(=O)OCCCC)C)C=C2)C=C1 Chemical compound ClC1=CC=C(OC2=CC=C(OC(C=CC(=O)OCCCC)C)C=C2)C=C1 YBWAKIKBIOTBEA-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- VJGNLOIQCWLBJR-UHFFFAOYSA-M benzyl(tributyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 VJGNLOIQCWLBJR-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
- MPCZUKWSZFWNBV-UHFFFAOYSA-M benzyl(tripentyl)azanium;chloride Chemical compound [Cl-].CCCCC[N+](CCCCC)(CCCCC)CC1=CC=CC=C1 MPCZUKWSZFWNBV-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006664 bond formation reaction Methods 0.000 description 1
- IKWKJIWDLVYZIY-UHFFFAOYSA-M butyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCC)C1=CC=CC=C1 IKWKJIWDLVYZIY-UHFFFAOYSA-M 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical compound ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 description 1
- 239000012351 deprotecting agent Substances 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- TZDXCVZSQCCGIV-UHFFFAOYSA-N ethyl 4-[4-(4-iodophenoxy)phenoxy]pent-2-enoate Chemical compound C1=CC(OC(C)C=CC(=O)OCC)=CC=C1OC1=CC=C(I)C=C1 TZDXCVZSQCCGIV-UHFFFAOYSA-N 0.000 description 1
- PJRFZMYESWZVFN-UHFFFAOYSA-N ethyl 4-[4-[2-(trifluoromethyl)phenoxy]phenoxy]pent-2-enoate Chemical compound C1=CC(OC(C)C=CC(=O)OCC)=CC=C1OC1=CC=CC=C1C(F)(F)F PJRFZMYESWZVFN-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- YTGHXYPZJCPPQS-UHFFFAOYSA-N hexadecylphosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[PH3+] YTGHXYPZJCPPQS-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000003112 potassium compounds Chemical class 0.000 description 1
- XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- SPALIFXDWQTXKS-UHFFFAOYSA-M tetrapentylazanium;bromide Chemical compound [Br-].CCCCC[N+](CCCCC)(CCCCC)CCCCC SPALIFXDWQTXKS-UHFFFAOYSA-M 0.000 description 1
- SXAWRMKQZKPHNJ-UHFFFAOYSA-M tetrapentylazanium;chloride Chemical compound [Cl-].CCCCC[N+](CCCCC)(CCCCC)CCCCC SXAWRMKQZKPHNJ-UHFFFAOYSA-M 0.000 description 1
- WAGFXJQAIZNSEQ-UHFFFAOYSA-M tetraphenylphosphonium chloride Chemical compound [Cl-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WAGFXJQAIZNSEQ-UHFFFAOYSA-M 0.000 description 1
- BGQMOFGZRJUORO-UHFFFAOYSA-M tetrapropylammonium bromide Chemical compound [Br-].CCC[N+](CCC)(CCC)CCC BGQMOFGZRJUORO-UHFFFAOYSA-M 0.000 description 1
- VBFVWBMHOSXZOX-UHFFFAOYSA-M tributyl(2-methylpropyl)azanium;bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CC(C)C VBFVWBMHOSXZOX-UHFFFAOYSA-M 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14028478A JPS5566531A (en) | 1978-11-14 | 1978-11-14 | Preparation of phenoxyalkene derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU182885B true HU182885B (en) | 1984-03-28 |
Family
ID=15265190
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU79IA861A HU182885B (en) | 1978-11-14 | 1979-11-12 | Process for preparing phenoxy-alkene derivatives |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS5566531A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
| HU (1) | HU182885B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5833216B2 (ja) * | 1978-12-12 | 1983-07-18 | クミアイ化学工業株式会社 | ４−（４−ハイドロキシフエノキシ）−２−ペンテン酸誘導体の製造法 |
-
1978
- 1978-11-14 JP JP14028478A patent/JPS5566531A/ja active Granted
-
1979
- 1979-11-12 HU HU79IA861A patent/HU182885B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6220971B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1987-05-11 |
| JPS5566531A (en) | 1980-05-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5021602A (en) | Reactive compounds containing perfluorocyclobutane rings | |
| EP0428709B1 (en) | Reactive compounds containing perfluorovinyl groups | |
| US2327053A (en) | Production of hydroxy ethers | |
| US3282979A (en) | Phenolic thioethers | |
| CA1293739C (en) | Process for preparing 2,2,3-trifluoropropionyl fluoride | |
| HU182584B (en) | Process for producing phenoxy-carboxylic acid derivatives | |
| HU182885B (en) | Process for preparing phenoxy-alkene derivatives | |
| JPH027933B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| AU641440B2 (en) | Alk-1-enyl ethers | |
| US4267317A (en) | Process for producing phenoxyalkene derivative | |
| CN1073934A (zh) | 新的合成2-羟基芳香醛化合物的方法 | |
| US5227533A (en) | Alk-1-enyl ethers | |
| KR820000947B1 (ko) | 페녹시알켄 유도체의 제조 방법 | |
| US4349487A (en) | Process for forming ethers | |
| US5281726A (en) | 4-hydroxy-2'-nitrobutyrophenone and tetrahydro-2-(o-nitrophenyl)-2-furanol useful as intermediates in the preparation of a crop-selective herbicide | |
| US5344986A (en) | Amino phenoxy compounds and process for their preparation | |
| CA1241344A (en) | Process for the preparation of halogenated 3,3- dimethyl-5-hexen-2-ones | |
| JP2513490B2 (ja) | アルキルチオベンズアルデヒド類の製造方法 | |
| US4450308A (en) | Process for the preparation of trifluoromethylphenyl oxyphenyl ether compounds | |
| US5101058A (en) | Fluorocarbon compounds and processes for preparation thereof | |
| JPH09188647A (ja) | アセトフェノン類の製造法 | |
| JP4371053B2 (ja) | グリシジルエーテル類の製造法 | |
| DK144791B (da) | Fremgangsmaade til fremstilling af 1,1-dihalogen-4-methyl-1,3-pentadiener | |
| US5185477A (en) | Halohydrin commpounds | |
| US5225606A (en) | Alk-1-enyl ethers |