SU457210A3 - Способ получени бензоил-/3-фенил/ -2-пропионовой или бензоил-/3-фенил/ -уксусной кислот - Google Patents
Способ получени бензоил-/3-фенил/ -2-пропионовой или бензоил-/3-фенил/ -уксусной кислотInfo
- Publication number
- SU457210A3 SU457210A3 SU1859757A SU1859757A SU457210A3 SU 457210 A3 SU457210 A3 SU 457210A3 SU 1859757 A SU1859757 A SU 1859757A SU 1859757 A SU1859757 A SU 1859757A SU 457210 A3 SU457210 A3 SU 457210A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- phenyl
- benzoyl
- propionic
- acid
- producing
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- MHKMCTCMEDUINO-UHFFFAOYSA-N 2-(3-benzoylphenyl)acetonitrile Chemical compound C=1C=CC(CC#N)=CC=1C(=O)C1=CC=CC=C1 MHKMCTCMEDUINO-UHFFFAOYSA-N 0.000 description 3
- -1 3-bromomethylenebenzophenone Chemical compound 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Chemical class 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000005171 halobenzenes Chemical class 0.000 description 2
- 229910052736 halogen Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000001953 recrystallisation Methods 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
- URBLVRAVOIVZFJ-UHFFFAOYSA-N (3-methylphenyl)-phenylmethanone Chemical compound CC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 URBLVRAVOIVZFJ-UHFFFAOYSA-N 0.000 description 1
- ALDSXDRDRWDASQ-UHFFFAOYSA-N 2-(3-benzoylphenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 ALDSXDRDRWDASQ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-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
- IGQHIUNZKLGBMZ-DJKKODMXSA-N Fc1ccc2c(OCc3ccccc3\C2=C/c2ccc3OCC(=O)Nc3c2)c1 Chemical compound Fc1ccc2c(OCc3ccccc3\C2=C/c2ccc3OCC(=O)Nc3c2)c1 IGQHIUNZKLGBMZ-DJKKODMXSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 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 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7143565A FR2163875A5 (en) | 1971-12-03 | 1971-12-03 | 3-benzoylphenyl acetic and 2-(3-benzoyl phenyl) - propionic acids prepn - for use as anti-inflammatories |
| FR7236570A FR2202873A2 (en) | 1972-10-16 | 1972-10-16 | 3-benzoylphenyl acetic and 2-(3-benzoyl phenyl) - propionic acids prepn - for use as anti-inflammatories |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU457210A3 true SU457210A3 (ru) | 1975-01-15 |
Family
ID=26216758
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1859757A SU457210A3 (ru) | 1971-12-03 | 1972-12-01 | Способ получени бензоил-/3-фенил/ -2-пропионовой или бензоил-/3-фенил/ -уксусной кислот |
Country Status (26)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2128160C1 (ru) * | 1992-11-10 | 1999-03-27 | Лабораториос Менарини С.А. | Трометаминная соль (+)-(s)-2-(3-бензоилфенил)пропионовой кислоты, способ ее получения, фармацевтическая композиция |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS582934B2 (ja) * | 1974-07-29 | 1983-01-19 | ニツシンセイフン カブシキガイシヤ | ２−（置換アリ−ル）−プロピオン酸の製法 |
| DE2708142C3 (de) * | 1977-02-25 | 1981-10-29 | Rütgerswerke AG, 6000 Frankfurt | Verfahren zur Herstellung von substituierten Phenylacetonitrilen und neue Phenylacetonitrile |
| EP0025262B1 (en) | 1979-07-16 | 1983-10-05 | Sagami Chemical Research Center | Alpha-thio-alpha-aryl-substituted alkanonitriles, process for their preparation, process for preparing alpha-aryl-substituted alkanonitriles and the corresponding carboxylic acids therefrom and process for preparing intermediates |
| SE8400239D0 (sv) * | 1984-01-19 | 1984-01-19 | Pharmacia Ab | Nya arylettiksyraderivat |
| ES2163986B1 (es) * | 1999-07-13 | 2003-02-16 | Menarini Lab | Acidos-alfa-arilpropionicos y arilaceticos como inhibidores de la ciclooxigenasa-ii. |
| CN111675631A (zh) * | 2020-06-24 | 2020-09-18 | 湖北仙盛科技股份有限公司 | 一种氰基酮洛芬合成工艺 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1546478A (fr) * | 1967-01-27 | 1968-11-22 | Rhone Poulenc Sa | Nouveaux dérivés de l'acide benzoyl-3 phénylacétique et leur préparation |
| GB1226344A (enrdf_load_stackoverflow) * | 1967-07-31 | 1971-03-24 |
-
1972
- 1972-11-22 OA OA54753A patent/OA04219A/xx unknown
- 1972-11-24 NL NL7215990A patent/NL7215990A/xx unknown
- 1972-11-30 IE IE1660/72A patent/IE36936B1/xx unknown
- 1972-11-30 JP JP47119468A patent/JPS528301B2/ja not_active Expired
- 1972-11-30 IL IL40972A patent/IL40972A/en unknown
- 1972-12-01 HU HURO687A patent/HU166290B/hu unknown
- 1972-12-01 NO NO4425/72A patent/NO139782C/no unknown
- 1972-12-01 SU SU1859757A patent/SU457210A3/ru active
- 1972-12-01 CH CH1756172A patent/CH545761A/xx not_active IP Right Cessation
- 1972-12-01 DD DD167245A patent/DD100239A5/xx unknown
- 1972-12-01 LU LU66586A patent/LU66586A1/xx unknown
- 1972-12-01 BE BE792218D patent/BE792218A/xx not_active IP Right Cessation
- 1972-12-01 AR AR245440A patent/AR194864A1/es active
- 1972-12-01 FI FI3415/72A patent/FI55173C/fi active
- 1972-12-01 CY CY916A patent/CY916A/xx unknown
- 1972-12-01 SE SE7215722A patent/SE397675B/xx unknown
- 1972-12-01 PL PL1972159227A patent/PL77271B1/pl unknown
- 1972-12-01 CA CA158,010A patent/CA972765A/en not_active Expired
- 1972-12-01 DE DE2258985A patent/DE2258985C2/de not_active Expired
- 1972-12-01 AT AT1022772A patent/AT321283B/de active
- 1972-12-01 DK DK602072AA patent/DK134814B/da not_active IP Right Cessation
- 1972-12-01 CS CS8228A patent/CS170457B2/cs unknown
- 1972-12-01 YU YU2990/72A patent/YU36003B/xx unknown
- 1972-12-01 GB GB5564072A patent/GB1360560A/en not_active Expired
- 1972-12-02 ES ES409237A patent/ES409237A1/es not_active Expired
-
1977
- 1977-12-01 HK HK601/77A patent/HK60177A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2128160C1 (ru) * | 1992-11-10 | 1999-03-27 | Лабораториос Менарини С.А. | Трометаминная соль (+)-(s)-2-(3-бензоилфенил)пропионовой кислоты, способ ее получения, фармацевтическая композиция |
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