JPH0545575B2 - - Google Patents
Info
- Publication number
- JPH0545575B2 JPH0545575B2 JP59189637A JP18963784A JPH0545575B2 JP H0545575 B2 JPH0545575 B2 JP H0545575B2 JP 59189637 A JP59189637 A JP 59189637A JP 18963784 A JP18963784 A JP 18963784A JP H0545575 B2 JPH0545575 B2 JP H0545575B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- general formula
- dihydric alcohol
- carbon atoms
- alkyl group
- 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 - Lifetime
Links
- 239000002253 acid Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 2
- 238000006462 rearrangement reaction Methods 0.000 claims 2
- 150000005846 sugar alcohols Polymers 0.000 claims 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- -1 cyclic acetal Chemical class 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 150000004679 hydroxides Chemical class 0.000 claims 1
- 150000003752 zinc compounds Chemical class 0.000 claims 1
- 235000014692 zinc oxide Nutrition 0.000 claims 1
- RNWHGQJWIACOKP-UHFFFAOYSA-N zinc;oxygen(2-) Chemical class [O-2].[Zn+2] RNWHGQJWIACOKP-UHFFFAOYSA-N 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000007513 acids 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
- 229960001680 ibuprofen Drugs 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
産業上の利用分野
本発明は、α−アリールアルカン酸の製造方法
に関するものである。詳しく述べると、一般式
Ar−CH（R3）COOHで表わされるα−アリール
アルカン酸の製造方法に関するものである。
従来の技術
前記一般式で表わされる化合物には薬理作用を
示すものが多く、例えば、Arがｐ−イソブチル
基でありかつR3がメチル基であるα−（ｐ−イソ
ブチルフエニル）プロピオン酸は、消炎剤、鎮痛
剤、下熱剤として有用な化合物であるイブプロフ
エンである。
従来、一般式Ar−CO−CH2CH3で表わされ
るアリールエチルケトンから一般式Ar−CH
（CH3）−COOHで表わされるα−アリールエタ
ン酸を得ようとする多くの試みがなされてきた。
その代表的な例は、つぎのようなものである。
(1) 特開昭54−5938号および特開昭54−5939号
INDUSTRIAL APPLICATION FIELD The present invention relates to a method for producing α-arylalkanoic acid. To be more specific, the general formula
The present invention relates to a method for producing α-arylalkanoic acid represented by Ar-CH(R 3 )COOH. PRIOR ART Many of the compounds represented by the above general formula exhibit pharmacological effects. For example, α-(p-isobutylphenyl)propionic acid in which Ar is a p-isobutyl group and R3 is a methyl group , ibuprofen, a compound useful as an anti-inflammatory, analgesic, and antipyretic agent. Conventionally, from the arylethyl ketone represented by the general formula Ar-CO-CH 2 CH 3 to the general formula Ar-CH
Many attempts have been made to obtain α-arylethanoic acids represented by (CH 3 )-COOH.
A typical example is as follows. (1) JP-A-54-5938 and JP-A-54-5939
【表】
｜
Ar−CHCOOCH３
NaOH CH３
｜
Ar−CH−COOH
HCl
RuまたはMn(AcO)３・4H２O
Tl()[Table] ｜
Ar−CHCOOCH 3
NaOHCH3
｜
Ar−CH−COOH
HCl
Ru or Mn(AcO) 3・4H 2 O
Tl()
Claims (1)
はアルキル基でありかつR1とR2とは一体となつ
て環状アセタールを形成し得るものも含み、R3
は水素原子またはアルキル基であり、またＸはハ
ロゲン原子である。）で表わされるα−ハロアル
キルアリールケタールを、亜鉛の酸化物、水酸化
物、炭酸塩および塩基性炭酸塩よりなる群から選
ばれた少なくとも１種の亜鉛化合物の存在下に、
炭素原子数２〜12の多価アルコールの少なくとも
１種よりなる希釈剤中で転位反応させ、ついで該
転位反応生成物を加水分解することを特徴とする
一般式 （ただし、式中、R3およびArは前記のとおりで
ある。）で表わされるα−アリールアルカン酸の
製造方法。 ２ 多価アルコールが二価アルコールである特許
請求の範囲第１項に記載の方法。 ３ 二価アルコールの炭素原子数が２〜４である
特許請求の範囲第２項に記載の方法。 ４ 二価アルコールがエチレングリコール、プロ
ピレングリコールまたはジエチレングリコールで
ある特許請求の範囲第３項に記載の方法。[Claims] 1. General formula (However, in the formula, Ar is an aromatic residue, R 1 and R 2
is an alkyl group, and R 1 and R 2 include those that can be combined to form a cyclic acetal, and R 3
is a hydrogen atom or an alkyl group, and X is a halogen atom. ) in the presence of at least one zinc compound selected from the group consisting of zinc oxides, hydroxides, carbonates and basic carbonates,
A general formula characterized by carrying out a rearrangement reaction in a diluent consisting of at least one polyhydric alcohol having 2 to 12 carbon atoms, and then hydrolyzing the rearrangement reaction product. (However, in the formula, R 3 and Ar are as described above.) A method for producing an α-arylalkanoic acid represented by the formula. 2. The method according to claim 1, wherein the polyhydric alcohol is a dihydric alcohol. 3. The method according to claim 2, wherein the dihydric alcohol has 2 to 4 carbon atoms. 4. The method according to claim 3, wherein the dihydric alcohol is ethylene glycol, propylene glycol or diethylene glycol.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59189637A JPS6168442A (en) | 1984-09-12 | 1984-09-12 | Production of alpha-arylalkanoic acid |
| US06/774,352 US4670586A (en) | 1984-09-12 | 1985-09-10 | Method for the production of α-aryl-alkanoic acid |
| EP85306454A EP0174844B1 (en) | 1984-09-12 | 1985-09-11 | Method for production of alpha-aryl-alkanoic acid |
| DE8585306454T DE3578417D1 (en) | 1984-09-12 | 1985-09-11 | METHOD FOR PRODUCING ALPHA ARYL ALKANIC ACIDS. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59189637A JPS6168442A (en) | 1984-09-12 | 1984-09-12 | Production of alpha-arylalkanoic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6168442A JPS6168442A (en) | 1986-04-08 |
| JPH0545575B2 true JPH0545575B2 (en) | 1993-07-09 |
Family
ID=16244629
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59189637A Granted JPS6168442A (en) | 1984-09-12 | 1984-09-12 | Production of alpha-arylalkanoic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6168442A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56135423A (en) * | 1980-02-26 | 1981-10-22 | Blasinachim Spa | Manufacture of alkanoic acid ester by rearrangement of alpha-haloketal and novel ketal compound |
| JPS5962545A (en) * | 1982-08-06 | 1984-04-10 | ザンボン・エス・ピ−・エ− | Manufacture of alpha-arylalkanoic acid |
-
1984
- 1984-09-12 JP JP59189637A patent/JPS6168442A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56135423A (en) * | 1980-02-26 | 1981-10-22 | Blasinachim Spa | Manufacture of alkanoic acid ester by rearrangement of alpha-haloketal and novel ketal compound |
| JPS5962545A (en) * | 1982-08-06 | 1984-04-10 | ザンボン・エス・ピ−・エ− | Manufacture of alpha-arylalkanoic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6168442A (en) | 1986-04-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4073822B2 (en) | Polymerization method of macrocyclic poly (alkylene dicarboxylate) oligomer | |
| ES8800069A1 (en) | Catalyst and process for producing alpha-olefin polymers using the same. | |
| JPS60136525A (en) | Production of ethanol | |
| KR850700133A (en) | Method of producing organic acid | |
| JPH05170701A (en) | Method of vinyl exchange by reactive distillation | |
| JPH09501691A (en) | Preparation of a mixture of alkyl pentanoates | |
| US4820862A (en) | Process for the preparation of dimethyl terephthalate | |
| JPH0545575B2 (en) | ||
| KR950003120B1 (en) | Improved process for preparing 5-(2,5-dimethyl phenoxy)-2,2-dimetheyl pentanoic acid | |
| JPH0545574B2 (en) | ||
| KR850005291A (en) | Preparation of ethylene glycol, preparation of catalyst composition and cocatalyst composition used therein | |
| JPS6069057A (en) | Manufacture of pure adipic acid monoester | |
| JP3413279B2 (en) | Phenolic hydroxyl group-containing lactone ring-opening polymer and method for producing the same | |
| JPS5527147A (en) | Preparation of carboxylic acid having aryl substituent | |
| JPS62114930A (en) | High yield carbonyl reaction of halo- hydrocarbon | |
| KR880011066A (en) | (Phenylethenyl) phenylpropionic acid and esters thereof and (benzoylphenyl) propionic acid or a method for producing the ester | |
| JPS61502125A (en) | chemical method | |
| WO2004108648A1 (en) | Method for preparing organic acid | |
| EP1215192A3 (en) | Preparation process of dicarboxylic acid compounds | |
| JPS60112738A (en) | Production of glyoxylic acid ester | |
| KR860004004A (en) | Method for preparing 4-acyloxy-3-oxo-butyric acid ester | |
| JP2006528227A (en) | Process for the hydrocarboxylation of ethylenically unsaturated carboxylic acids | |
| CA1202319A (en) | Process for the preparation of diphenyl ether derivatives | |
| EP0402063A3 (en) | Alpha-(omega-cyanoalkanoyl)-gamma-butyrolactone and method for producing the same | |
| US3917662A (en) | Preparation of fatty acid esters |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| EXPY | Cancellation because of completion of term |