JPS625919B2 - - Google Patents

Info

Publication number

JPS625919B2

JPS625919B2 JP50023775A JP2377575A JPS625919B2 JP S625919 B2 JPS625919 B2 JP S625919B2 JP 50023775 A JP50023775 A JP 50023775A JP 2377575 A JP2377575 A JP 2377575A JP S625919 B2 JPS625919 B2 JP S625919B2

Authority

JP

Japan

Prior art keywords

group

acid

mixture

add

methoxy

Prior art date

1974-02-26

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired

Links

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• 239000000203 mixture Substances 0.000 claims description 261
• -1 amino, amino Chemical group 0.000 claims description 216
• 150000001875 compounds Chemical class 0.000 claims description 133
• 150000003839 salts Chemical class 0.000 claims description 92
• 238000000034 method Methods 0.000 claims description 67
• 125000003545 alkoxy group Chemical group 0.000 claims description 53
• 125000000217 alkyl group Chemical group 0.000 claims description 43
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 38
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
• 125000003118 aryl group Chemical group 0.000 claims description 15
• SXBDXXFTJVHSAF-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-3-en-8-one Chemical class S1C=CCN2C(=O)C[C@H]21 SXBDXXFTJVHSAF-ZCFIWIBFSA-N 0.000 claims description 12
• 229910052736 halogen Inorganic materials 0.000 claims description 11
• 229910052739 hydrogen Inorganic materials 0.000 claims description 10
• 239000001257 hydrogen Substances 0.000 claims description 9
• 238000004519 manufacturing process Methods 0.000 claims description 9
• 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 8
• 125000005103 alkyl silyl group Chemical group 0.000 claims description 7
• 150000002367 halogens Chemical class 0.000 claims description 7
• 150000002431 hydrogen Chemical group 0.000 claims description 7
• 125000001544 thienyl group Chemical group 0.000 claims description 7
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
• 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims description 6
• FZEVMBJWXHDLDB-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical compound S1CC=CN2C(=O)C[C@H]21 FZEVMBJWXHDLDB-ZCFIWIBFSA-N 0.000 claims description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 431
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 293
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 277
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 189
• 239000000243 solution Substances 0.000 description 166
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 134
• 238000003756 stirring Methods 0.000 description 129
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 111
• 235000019439 ethyl acetate Nutrition 0.000 description 97
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 93
• 239000000741 silica gel Substances 0.000 description 79
• 229910002027 silica gel Inorganic materials 0.000 description 79
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 77
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 74
• 239000002253 acid Substances 0.000 description 68
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
• 238000002844 melting Methods 0.000 description 59
• 230000008018 melting Effects 0.000 description 59
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 58
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 53
• 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 52
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 51
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 50
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 47
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 45
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 44
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 44
• 238000002329 infrared spectrum Methods 0.000 description 44
• 229910052938 sodium sulfate Inorganic materials 0.000 description 44
• 235000011152 sodium sulphate Nutrition 0.000 description 44
• 239000002904 solvent Substances 0.000 description 42
• 229960000583 acetic acid Drugs 0.000 description 41
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 40
• 239000002994 raw material Substances 0.000 description 40
• 238000006243 chemical reaction Methods 0.000 description 38
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 38
• 239000012074 organic phase Substances 0.000 description 38
• 150000002148 esters Chemical class 0.000 description 36
• 235000019441 ethanol Nutrition 0.000 description 35
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 34
• 239000010410 layer Substances 0.000 description 32
• 239000007864 aqueous solution Substances 0.000 description 28
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 27
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
• 229910001873 dinitrogen Inorganic materials 0.000 description 26
• 150000004702 methyl esters Chemical class 0.000 description 26
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
• 229910001385 heavy metal Inorganic materials 0.000 description 25
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 25
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 24
• 235000017557 sodium bicarbonate Nutrition 0.000 description 24
• 239000003795 chemical substances by application Substances 0.000 description 23
• 239000002244 precipitate Substances 0.000 description 23
• QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 22
• 239000000047 product Substances 0.000 description 22
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 21
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 21
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 21
• 239000008346 aqueous phase Substances 0.000 description 21
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 21
• 239000011541 reaction mixture Substances 0.000 description 21
• 239000011780 sodium chloride Substances 0.000 description 21
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 19
• 239000002585 base Substances 0.000 description 19
• 239000000284 extract Substances 0.000 description 19
• 125000001931 aliphatic group Chemical group 0.000 description 18
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 18
• 239000012141 concentrate Substances 0.000 description 17
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
• 125000005843 halogen group Chemical group 0.000 description 16
• 239000000126 substance Substances 0.000 description 16
• 229910052801 chlorine Inorganic materials 0.000 description 15
• 239000000706 filtrate Substances 0.000 description 15
• 239000013078 crystal Substances 0.000 description 14
• 239000012071 phase Substances 0.000 description 14
• 229920006395 saturated elastomer Polymers 0.000 description 14
• 238000001228 spectrum Methods 0.000 description 14
• YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 13
• 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 13
• 125000004432 carbon atom Chemical group C* 0.000 description 13
• 229910052708 sodium Inorganic materials 0.000 description 13
• LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 13
• 238000002211 ultraviolet spectrum Methods 0.000 description 13
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 12
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 12
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 12
• 239000012043 crude product Substances 0.000 description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
• 235000019253 formic acid Nutrition 0.000 description 12
• SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 12
• 239000011734 sodium Substances 0.000 description 12
• 235000015424 sodium Nutrition 0.000 description 12
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 11
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 11
• 230000002378 acidificating effect Effects 0.000 description 11
• 239000004305 biphenyl Substances 0.000 description 11
• 239000000460 chlorine Substances 0.000 description 11
• 238000000354 decomposition reaction Methods 0.000 description 11
• 229910052757 nitrogen Inorganic materials 0.000 description 11
• 239000007787 solid Substances 0.000 description 11
• CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 10
• KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 10
• RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 10
• 125000001309 chloro group Chemical group Cl* 0.000 description 10
• 238000004587 chromatography analysis Methods 0.000 description 10
• 238000004809 thin layer chromatography Methods 0.000 description 10
• KWPQTFXULUUCGD-UHFFFAOYSA-N 3,4,5,7,8,9,10,10a-octahydropyrido[1,2-a][1,4]diazepine Chemical compound C1CCN=CC2CCCCN21 KWPQTFXULUUCGD-UHFFFAOYSA-N 0.000 description 9
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 9
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
• 229920002472 Starch Polymers 0.000 description 9
• 238000000862 absorption spectrum Methods 0.000 description 9
• 150000001335 aliphatic alkanes Chemical class 0.000 description 9
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 9
• 229910052799 carbon Inorganic materials 0.000 description 9
• 150000002168 ethanoic acid esters Chemical class 0.000 description 9
• 229910052731 fluorine Inorganic materials 0.000 description 9
• QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 description 9
• 239000012362 glacial acetic acid Substances 0.000 description 9
• 239000007788 liquid Substances 0.000 description 9
• 238000002156 mixing Methods 0.000 description 9
• 125000001424 substituent group Chemical group 0.000 description 9
• NGCRXXLKJAAUQQ-UHFFFAOYSA-N undec-5-ene Chemical compound CCCCCC=CCCCC NGCRXXLKJAAUQQ-UHFFFAOYSA-N 0.000 description 9
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 8
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
• 150000007513 acids Chemical class 0.000 description 8
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
• 239000011737 fluorine Substances 0.000 description 8
• DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 description 8
• 229910052740 iodine Inorganic materials 0.000 description 8
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
• 235000019341 magnesium sulphate Nutrition 0.000 description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
• 229910052760 oxygen Inorganic materials 0.000 description 8
• 239000001301 oxygen Substances 0.000 description 8
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
• 125000006239 protecting group Chemical group 0.000 description 8
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
• YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 7
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 7
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
• 150000001412 amines Chemical class 0.000 description 7
• 235000010290 biphenyl Nutrition 0.000 description 7
• 229910052794 bromium Inorganic materials 0.000 description 7
• 239000000499 gel Substances 0.000 description 7
• 239000005457 ice water Substances 0.000 description 7
• 239000011630 iodine Substances 0.000 description 7
• LDHQCZJRKDOVOX-IHWYPQMZSA-N isocrotonic acid Chemical group C\C=C/C(O)=O LDHQCZJRKDOVOX-IHWYPQMZSA-N 0.000 description 7
• 229910052751 metal Inorganic materials 0.000 description 7
• 239000002184 metal Substances 0.000 description 7
• JWHOQZUREKYPBY-UHFFFAOYSA-N rubonic acid Natural products CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CC(=O)C34C)C2C1)C(=O)O JWHOQZUREKYPBY-UHFFFAOYSA-N 0.000 description 7
• 229910052709 silver Inorganic materials 0.000 description 7
• 239000004332 silver Substances 0.000 description 7
• CPXGFFUFUXXZGC-UHFFFAOYSA-M silver;4-methylbenzenesulfinate Chemical compound [Ag+].CC1=CC=C(S([O-])=O)C=C1 CPXGFFUFUXXZGC-UHFFFAOYSA-M 0.000 description 7
• 235000011121 sodium hydroxide Nutrition 0.000 description 7
• 239000008107 starch Substances 0.000 description 7
• 235000019698 starch Nutrition 0.000 description 7
• GWIKYPMLNBTJHR-UHFFFAOYSA-M thiosulfonate group Chemical group S(=S)(=O)[O-] GWIKYPMLNBTJHR-UHFFFAOYSA-M 0.000 description 7
• 239000000052 vinegar Substances 0.000 description 7
• 235000021419 vinegar Nutrition 0.000 description 7
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 6
• 125000002252 acyl group Chemical group 0.000 description 6
• 229910052783 alkali metal Inorganic materials 0.000 description 6
• HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 6
• 150000001768 cations Chemical class 0.000 description 6
• NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 6
• 238000001816 cooling Methods 0.000 description 6
• 238000006266 etherification reaction Methods 0.000 description 6
• 238000010438 heat treatment Methods 0.000 description 6
• 239000000155 melt Substances 0.000 description 6
• 125000004433 nitrogen atom Chemical group N* 0.000 description 6
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
• 239000003921 oil Substances 0.000 description 6
• WURFKUQACINBSI-UHFFFAOYSA-M ozonide Chemical compound [O]O[O-] WURFKUQACINBSI-UHFFFAOYSA-M 0.000 description 6
• 239000003208 petroleum Substances 0.000 description 6
• FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 6
• 229910052700 potassium Inorganic materials 0.000 description 6
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
• 150000003254 radicals Chemical class 0.000 description 6
• 238000001953 recrystallisation Methods 0.000 description 6
• 238000010992 reflux Methods 0.000 description 6
• 229910001961 silver nitrate Inorganic materials 0.000 description 6
• 239000011877 solvent mixture Substances 0.000 description 6
• 239000000725 suspension Substances 0.000 description 6
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
• 230000001256 tonic effect Effects 0.000 description 6
• DILXLMRYFWFBGR-UHFFFAOYSA-N 2-formylbenzene-1,4-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(S(O)(=O)=O)C(C=O)=C1 DILXLMRYFWFBGR-UHFFFAOYSA-N 0.000 description 5
• 239000005973 Carvone Substances 0.000 description 5
• DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 5
• 150000003973 alkyl amines Chemical class 0.000 description 5
• 125000005907 alkyl ester group Chemical group 0.000 description 5
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 5
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
• 238000001704 evaporation Methods 0.000 description 5
• 230000008020 evaporation Effects 0.000 description 5
• 125000000623 heterocyclic group Chemical group 0.000 description 5
• 239000011261 inert gas Substances 0.000 description 5
• 239000000543 intermediate Substances 0.000 description 5
• 239000000463 material Substances 0.000 description 5
• UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 5
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 5
• 150000007522 mineralic acids Chemical class 0.000 description 5
• 125000002950 monocyclic group Chemical group 0.000 description 5
• 239000012452 mother liquor Substances 0.000 description 5
• 239000011591 potassium Substances 0.000 description 5
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