TW201305104A - ３－氯－４－甲基苯甲酸異丙酯及其製造方法 - Google Patents
３－氯－４－甲基苯甲酸異丙酯及其製造方法 Download PDFInfo
- Publication number
- TW201305104A TW201305104A TW101124026A TW101124026A TW201305104A TW 201305104 A TW201305104 A TW 201305104A TW 101124026 A TW101124026 A TW 101124026A TW 101124026 A TW101124026 A TW 101124026A TW 201305104 A TW201305104 A TW 201305104A
- Authority
- TW
- Taiwan
- Prior art keywords
- chloro
- methylbenzoic acid
- reaction
- isopropyl
- methylbenzoate
- Prior art date
Links
- RODCVSHNESCUTL-UHFFFAOYSA-N propan-2-yl 3-chloro-4-methylbenzoate Chemical compound CC(C)OC(=O)C1=CC=C(C)C(Cl)=C1 RODCVSHNESCUTL-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 238000004519 manufacturing process Methods 0.000 title abstract description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 55
- 238000005660 chlorination reaction Methods 0.000 claims abstract description 20
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000000460 chlorine Substances 0.000 claims abstract description 9
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 9
- 239000011968 lewis acid catalyst Substances 0.000 claims abstract description 7
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 claims description 36
- SDKUOEOJAXGCLU-UHFFFAOYSA-N 3-chloro-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1Cl SDKUOEOJAXGCLU-UHFFFAOYSA-N 0.000 claims description 33
- 238000003756 stirring Methods 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 14
- GANDSBWEBNXLMG-UHFFFAOYSA-N 3-chloro-4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1Cl GANDSBWEBNXLMG-UHFFFAOYSA-N 0.000 abstract description 11
- 230000015572 biosynthetic process Effects 0.000 abstract description 11
- 229920001002 functional polymer Polymers 0.000 abstract description 5
- 239000002861 polymer material Substances 0.000 abstract description 5
- 238000003786 synthesis reaction Methods 0.000 abstract description 5
- 239000003814 drug Substances 0.000 abstract description 3
- ZKGMMYWJFPYTGQ-UHFFFAOYSA-N 4-chloro-2-methylbenzoyl chloride Chemical compound CC1=CC(Cl)=CC=C1C(Cl)=O ZKGMMYWJFPYTGQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003905 agrochemical Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 45
- 239000002994 raw material Substances 0.000 description 19
- 238000004821 distillation Methods 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 16
- 238000005886 esterification reaction Methods 0.000 description 11
- 239000000543 intermediate Substances 0.000 description 11
- -1 propyl 3-chloro-4-methylbenzoic acid isopropyl ester Chemical compound 0.000 description 10
- 239000007789 gas Substances 0.000 description 9
- 239000012535 impurity Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 7
- 229940126214 compound 3 Drugs 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 229940125782 compound 2 Drugs 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000575 pesticide Substances 0.000 description 6
- PKLKKNXHDDASGV-UHFFFAOYSA-N propan-2-yl 5-chloro-4-methyl-2-nitrobenzoate Chemical compound CC(C)OC(=O)C1=CC(Cl)=C(C)C=C1[N+]([O-])=O PKLKKNXHDDASGV-UHFFFAOYSA-N 0.000 description 6
- 150000001491 aromatic compounds Chemical group 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000003963 dichloro group Chemical group Cl* 0.000 description 3
- 229940117389 dichlorobenzene Drugs 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- 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 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 230000006911 nucleation Effects 0.000 description 2
- 238000010899 nucleation Methods 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
- 238000002360 preparation method Methods 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 239000013076 target substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 1
- DMHZDOTYAVHSEH-UHFFFAOYSA-N 1-(chloromethyl)-4-methylbenzene Chemical compound CC1=CC=C(CCl)C=C1 DMHZDOTYAVHSEH-UHFFFAOYSA-N 0.000 description 1
- ZHJOQLHRCOXPLV-UHFFFAOYSA-N 1-chloro-2-methylbenzene;hydrochloride Chemical compound Cl.CC1=CC=CC=C1Cl ZHJOQLHRCOXPLV-UHFFFAOYSA-N 0.000 description 1
- PBUDJTSPOLSTQE-UHFFFAOYSA-N 2,3-dichloro-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C(Cl)=C1Cl PBUDJTSPOLSTQE-UHFFFAOYSA-N 0.000 description 1
- JTMYLQKKQFLIGV-UHFFFAOYSA-N 2-chloro-4-(chloromethyl)-1-methylbenzene Chemical compound CC1=CC=C(CCl)C=C1Cl JTMYLQKKQFLIGV-UHFFFAOYSA-N 0.000 description 1
- MYJUBDJLKREUGU-UHFFFAOYSA-N 2-chloro-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C(Cl)=C1 MYJUBDJLKREUGU-UHFFFAOYSA-N 0.000 description 1
- 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 1
- AFGAORZJNYXGEV-UHFFFAOYSA-N 5-chloro-4-methyl-2-nitrobenzoic acid Chemical compound CC1=CC([N+]([O-])=O)=C(C(O)=O)C=C1Cl AFGAORZJNYXGEV-UHFFFAOYSA-N 0.000 description 1
- 238000006418 Brown reaction Methods 0.000 description 1
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 1
- FEXQDZTYJVXMOS-UHFFFAOYSA-N Isopropyl benzoate Chemical compound CC(C)OC(=O)C1=CC=CC=C1 FEXQDZTYJVXMOS-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2011165361A JP2013028559A (ja) | 2011-07-28 | 2011-07-28 | ３−クロロ−４−メチル安息香酸イソプロピル及びその製造方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW201305104A true TW201305104A (zh) | 2013-02-01 |
Family
ID=47601050
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW101124026A TW201305104A (zh) | 2011-07-28 | 2012-07-04 | ３－氯－４－甲基苯甲酸異丙酯及其製造方法 |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP2013028559A (enExample) |
| CN (1) | CN103917515A (enExample) |
| TW (1) | TW201305104A (enExample) |
| WO (1) | WO2013015203A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108218708B (zh) * | 2016-12-15 | 2021-01-05 | 利尔化学股份有限公司 | 5-氯-4-甲基-2-硝基苯甲酸的制备方法及其用途 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8400254D0 (en) * | 1984-01-06 | 1984-02-08 | Searle & Co | Substituted alklidene imidazoles |
| JP2527961B2 (ja) * | 1987-04-24 | 1996-08-28 | 日本農薬株式会社 | 安息香酸エステル誘導体及びその製造方法 |
| DE4339208A1 (de) * | 1993-11-17 | 1995-05-18 | Hoechst Ag | Verfahren zur Herstellung von Fluorbenzoesäurealkylestern in hoher Reinheit und Ausbeute |
| JPH07330663A (ja) * | 1994-06-08 | 1995-12-19 | Nippon Light Metal Co Ltd | ２−クロロテレフタル酸クロライドの製造方法 |
| EP0995742A4 (en) * | 1997-06-27 | 2004-08-25 | Fujisawa Pharmaceutical Co | SULPHONAMIDE COMPOUNDS AND THEIR MEDICAL USE |
| WO1999016743A1 (en) * | 1997-09-30 | 1999-04-08 | Korea Research Institute Of Chemical Technology | A PROCESS FOR PREPARING o-(CARBOALKOXY) PHENYLMETHANESULFONYL CHLORIDE DERIVATIVES |
| ITMI20020974A1 (it) * | 2002-05-09 | 2003-11-10 | Miteni Spa | Procedimento per la preparazione dell'acido 4-fluoro-antranilico |
| US20040132726A1 (en) * | 2002-08-09 | 2004-07-08 | Astrazeneca Ab And Nps Pharmaceuticals, Inc. | New compounds |
| CN1762970A (zh) * | 2005-09-13 | 2006-04-26 | 上海大学 | 羧酸酯的合成方法 |
| DE102005050376A1 (de) * | 2005-10-21 | 2007-05-31 | Bayer Healthcare Ag | Dicarbonsäure-Derivate und ihre Verwendung |
| JP5558352B2 (ja) * | 2008-07-15 | 2014-07-23 | 日本化薬株式会社 | ６−アリールオキシキノリン誘導体の製造方法およびその中間体 |
-
2011
- 2011-07-28 JP JP2011165361A patent/JP2013028559A/ja active Pending
-
2012
- 2012-07-04 TW TW101124026A patent/TW201305104A/zh unknown
- 2012-07-20 CN CN201280036985.2A patent/CN103917515A/zh active Pending
- 2012-07-20 WO PCT/JP2012/068409 patent/WO2013015203A1/ja not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| CN103917515A (zh) | 2014-07-09 |
| WO2013015203A1 (ja) | 2013-01-31 |
| JP2013028559A (ja) | 2013-02-07 |
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