CA1142957A - PROCESS FOR PREPARING .alpha.-ARYL PROPIONIC ACIDS - Google Patents
PROCESS FOR PREPARING .alpha.-ARYL PROPIONIC ACIDSInfo
- Publication number
- CA1142957A CA1142957A CA000356361A CA356361A CA1142957A CA 1142957 A CA1142957 A CA 1142957A CA 000356361 A CA000356361 A CA 000356361A CA 356361 A CA356361 A CA 356361A CA 1142957 A CA1142957 A CA 1142957A
- Authority
- CA
- Canada
- Prior art keywords
- aryl
- formula
- ketone
- alpha
- preparing
- 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.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract 3
- 150000004672 propanoic acids Chemical class 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- 235000019260 propionic acid Nutrition 0.000 claims abstract description 7
- 229960000583 acetic acid Drugs 0.000 claims abstract description 5
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 5
- 239000012362 glacial acetic acid Substances 0.000 claims abstract description 4
- 101100006371 Arabidopsis thaliana CHX3 gene Proteins 0.000 claims abstract 3
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract 2
- 150000002576 ketones Chemical class 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000003426 co-catalyst Substances 0.000 claims description 3
- 125000003172 aldehyde group Chemical group 0.000 claims description 2
- VUEDNLCYHKSELL-UHFFFAOYSA-N arsonium Chemical group [AsH4+] VUEDNLCYHKSELL-UHFFFAOYSA-N 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 229910000000 metal hydroxide Inorganic materials 0.000 claims 2
- 150000004692 metal hydroxides Chemical class 0.000 claims 2
- 150000003254 radicals Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000003054 catalyst Substances 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 5
- 238000003756 stirring Methods 0.000 description 5
- -1 Li S04 Chemical class 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000004310 lactic acid Substances 0.000 description 4
- TZSHABFTBBOGRG-UHFFFAOYSA-N 2-hydroxy-2-(6-methoxynaphthalen-2-yl)propanoic acid Chemical compound C1=C(C(C)(O)C(O)=O)C=CC2=CC(OC)=CC=C21 TZSHABFTBBOGRG-UHFFFAOYSA-N 0.000 description 3
- 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000005840 aryl radicals Chemical class 0.000 description 3
- 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 3
- 229950005228 bromoform Drugs 0.000 description 3
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 238000003476 Darzens condensation reaction Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
- KLECYOQFQXJYBC-UHFFFAOYSA-N 1-fluoro-2-phenylbenzene Chemical group FC1=CC=CC=C1C1=CC=CC=C1 KLECYOQFQXJYBC-UHFFFAOYSA-N 0.000 description 1
- FVABNGAWNULIKN-UHFFFAOYSA-N 2-hydroxy-3,3-dimethoxy-2-naphthalen-2-ylpropanoic acid Chemical compound COC(C(C(=O)O)(O)C=1C=C2C=CC=CC2=CC1)OC FVABNGAWNULIKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 229940125716 antipyretic agent Drugs 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229960002390 flurbiprofen Drugs 0.000 description 1
- SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229960002009 naproxen Drugs 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical group 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- YSCDGVXAUXZABT-UHFFFAOYSA-N triacetylazanium;chloride Chemical compound [Cl-].CC(=O)[NH+](C(C)=O)C(C)=O YSCDGVXAUXZABT-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT24420/79A IT1122202B (it) | 1979-07-17 | 1979-07-17 | Processo per la preparazione di acidi alfa-aril propionici |
| IT24420A/79 | 1979-07-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1142957A true CA1142957A (en) | 1983-03-15 |
Family
ID=11213452
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000356361A Expired CA1142957A (en) | 1979-07-17 | 1980-07-16 | PROCESS FOR PREPARING .alpha.-ARYL PROPIONIC ACIDS |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5616437A (en, 2012) |
| AR (1) | AR225317A1 (en, 2012) |
| CA (1) | CA1142957A (en, 2012) |
| ES (1) | ES494168A0 (en, 2012) |
| GB (1) | GB2055814B (en, 2012) |
| IT (1) | IT1122202B (en, 2012) |
| YU (1) | YU182480A (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0591953A (ja) * | 1991-10-03 | 1993-04-16 | Yukihiro Kuwamoto | 木製浴槽、並びに木製浴槽の施工方法 |
| IT1298267B1 (it) * | 1998-02-18 | 1999-12-20 | Zambon Spa | Procedimento per la preparazione dell'acido (s)-2-acetiltio-3-fenil- propionico e dei suoi sali |
| JP7345777B2 (ja) * | 2019-06-11 | 2023-09-19 | 国立大学法人千葉大学 | ケトン化合物の製造方法、カルボン酸誘導体の製造方法 |
-
1979
- 1979-07-17 IT IT24420/79A patent/IT1122202B/it active
-
1980
- 1980-02-20 JP JP1931380A patent/JPS5616437A/ja active Granted
- 1980-07-03 GB GB8021800A patent/GB2055814B/en not_active Expired
- 1980-07-15 YU YU01824/80A patent/YU182480A/xx unknown
- 1980-07-15 ES ES494168A patent/ES494168A0/es active Granted
- 1980-07-16 CA CA000356361A patent/CA1142957A/en not_active Expired
- 1980-07-17 AR AR281798A patent/AR225317A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5616437A (en) | 1981-02-17 |
| AR225317A1 (es) | 1982-03-15 |
| ES8106269A1 (es) | 1981-08-01 |
| JPS6252736B2 (en, 2012) | 1987-11-06 |
| GB2055814B (en) | 1983-09-07 |
| IT1122202B (it) | 1986-04-23 |
| YU182480A (en) | 1983-01-21 |
| ES494168A0 (es) | 1981-08-01 |
| IT7924420A0 (it) | 1979-07-17 |
| GB2055814A (en) | 1981-03-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |