JPS60204742A - テトラフルオロ−４−ヒドロキシ安息香酸の製法 - Google Patents
テトラフルオロ−４−ヒドロキシ安息香酸の製法Info
- Publication number
- JPS60204742A JPS60204742A JP6101684A JP6101684A JPS60204742A JP S60204742 A JPS60204742 A JP S60204742A JP 6101684 A JP6101684 A JP 6101684A JP 6101684 A JP6101684 A JP 6101684A JP S60204742 A JPS60204742 A JP S60204742A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- tetrafluoro
- aqueous solution
- hydroxybenzoic acid
- alkaline substance
- Prior art date
- 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.)
- Granted
Links
- FTLHGQOBAPTEHE-UHFFFAOYSA-N 2,3,5,6-tetrafluoro-4-hydroxybenzoic acid Chemical compound OC(=O)C1=C(F)C(F)=C(O)C(F)=C1F FTLHGQOBAPTEHE-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 239000007864 aqueous solution Substances 0.000 claims abstract description 20
- 239000000126 substance Substances 0.000 claims abstract description 15
- MEXUTNIFSHFQRG-UHFFFAOYSA-N 6,7,12,13-tetrahydro-5h-indolo[2,3-a]pyrrolo[3,4-c]carbazol-5-one Chemical compound C12=C3C=CC=C[C]3NC2=C2NC3=CC=C[CH]C3=C2C2=C1C(=O)NC2 MEXUTNIFSHFQRG-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 8
- 230000002378 acidificating effect Effects 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 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 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 150000007514 bases Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002253 acid Substances 0.000 abstract description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 4
- 239000010410 layer Substances 0.000 abstract description 4
- 239000012044 organic layer Substances 0.000 abstract description 3
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 abstract description 2
- 238000000746 purification Methods 0.000 abstract description 2
- 238000001953 recrystallisation Methods 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 3
- 238000000151 deposition Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 150000001447 alkali salts Chemical class 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000003916 acid precipitation Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- BTXKLSXOHABRQQ-UHFFFAOYSA-N 2,3,5,6-tetrafluoro-4-hydroxybenzoic acid;hydrate Chemical compound O.OC(=O)C1=C(F)C(F)=C(O)C(F)=C1F BTXKLSXOHABRQQ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- WKYGDMSOKGXAAY-UHFFFAOYSA-N 2,3,4,5-tetrafluoro-6-hydroxybenzoic acid Chemical compound OC(=O)C1=C(O)C(F)=C(F)C(F)=C1F WKYGDMSOKGXAAY-UHFFFAOYSA-N 0.000 description 1
- QXYLYYZZWZQACI-UHFFFAOYSA-N 2,3,4,5-tetrafluorophenol Chemical compound OC1=CC(F)=C(F)C(F)=C1F QXYLYYZZWZQACI-UHFFFAOYSA-N 0.000 description 1
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- NXWTWYULZRDBSA-UHFFFAOYSA-N 2-fluoro-4-hydroxybenzoic acid Chemical class OC(=O)C1=CC=C(O)C=C1F NXWTWYULZRDBSA-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- FRMWBRPWYBNAFB-UHFFFAOYSA-M potassium salicylate Chemical compound [K+].OC1=CC=CC=C1C([O-])=O FRMWBRPWYBNAFB-UHFFFAOYSA-M 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- -1 tetrafluoro-4-hydroxybenzoin Chemical compound 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6101684A JPS60204742A (ja) | 1984-03-30 | 1984-03-30 | テトラフルオロ−４−ヒドロキシ安息香酸の製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6101684A JPS60204742A (ja) | 1984-03-30 | 1984-03-30 | テトラフルオロ−４−ヒドロキシ安息香酸の製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60204742A true JPS60204742A (ja) | 1985-10-16 |
| JPS6316375B2 JPS6316375B2 (enExample) | 1988-04-08 |
Family
ID=13159100
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6101684A Granted JPS60204742A (ja) | 1984-03-30 | 1984-03-30 | テトラフルオロ−４−ヒドロキシ安息香酸の製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60204742A (enExample) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63264439A (ja) * | 1986-12-08 | 1988-11-01 | Ube Ind Ltd | ３，５，６−トリフルオロ−４−ヒドロキシフタル酸の製造法 |
| JPH02225438A (ja) * | 1989-02-28 | 1990-09-07 | Nippon Shokubai Kagaku Kogyo Co Ltd | ２，３，５，６―テトラフルオロ―４―ヒドロキシ安息香酸の製造方法 |
| EP0602549A1 (de) * | 1992-12-17 | 1994-06-22 | Hoechst Aktiengesellschaft | 4-Hydroxy-2,3,5-trifluorbenzoesäure und Verfahren zu ihrer Herstellung |
| EP0894784A4 (en) * | 1996-10-18 | 1999-12-01 | Ihara Chemical Ind Co | 4-FLUOROSALICYCLIC ACID DERIVATIVES AND THEIR PRODUCTION METHOD |
| CN112979424A (zh) * | 2020-11-26 | 2021-06-18 | 浙江中欣氟材股份有限公司 | 一种含氟苯酚结构化合物的合成方法 |
-
1984
- 1984-03-30 JP JP6101684A patent/JPS60204742A/ja active Granted
Non-Patent Citations (1)
| Title |
|---|
| ZHURNAL OBSHCHEI KHIMII=1969 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63264439A (ja) * | 1986-12-08 | 1988-11-01 | Ube Ind Ltd | ３，５，６−トリフルオロ−４−ヒドロキシフタル酸の製造法 |
| JPH02225438A (ja) * | 1989-02-28 | 1990-09-07 | Nippon Shokubai Kagaku Kogyo Co Ltd | ２，３，５，６―テトラフルオロ―４―ヒドロキシ安息香酸の製造方法 |
| EP0602549A1 (de) * | 1992-12-17 | 1994-06-22 | Hoechst Aktiengesellschaft | 4-Hydroxy-2,3,5-trifluorbenzoesäure und Verfahren zu ihrer Herstellung |
| US5446198A (en) * | 1992-12-17 | 1995-08-29 | Hoechst Aktiengesellschaft | 4-hydroxy-2,3,5-trifluorobenzoic acid and a process for its preparation |
| EP0894784A4 (en) * | 1996-10-18 | 1999-12-01 | Ihara Chemical Ind Co | 4-FLUOROSALICYCLIC ACID DERIVATIVES AND THEIR PRODUCTION METHOD |
| CN112979424A (zh) * | 2020-11-26 | 2021-06-18 | 浙江中欣氟材股份有限公司 | 一种含氟苯酚结构化合物的合成方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6316375B2 (enExample) | 1988-04-08 |
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