FR2383912A1 - PROCESS FOR PREPARATION OF A DIESTER OF A-ACETYL-A'-METHYLSUCCINIC ACID - Google Patents

PROCESS FOR PREPARATION OF A DIESTER OF A-ACETYL-A'-METHYLSUCCINIC ACID

Info

Publication number
FR2383912A1
FR2383912A1 FR7807636A FR7807636A FR2383912A1 FR 2383912 A1 FR2383912 A1 FR 2383912A1 FR 7807636 A FR7807636 A FR 7807636A FR 7807636 A FR7807636 A FR 7807636A FR 2383912 A1 FR2383912 A1 FR 2383912A1
Authority
FR
France
Prior art keywords
preparation
alpha
diester
acetyl
methylsuccinic acid
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.)
Withdrawn
Application number
FR7807636A
Other languages
French (fr)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Pharmacia and Upjohn Co
Original Assignee
Upjohn Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Upjohn Co filed Critical Upjohn Co
Publication of FR2383912A1 publication Critical patent/FR2383912A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • C07C69/716—Esters of keto-carboxylic acids or aldehydo-carboxylic acids

Abstract

L'invention concerne un procédé de préparation d'un diester d'acide alpha -acétyl- alpha '-méthylsuccinique. Le produit est obtenu par un procédé qui minimise la décomposition de ce diester par reaction d'un acétylacétate avec un alpha -halogénopropionate dans un solvant contenant un liquide aprotique non polaire à une température d'environ 50 degrés C à la température de reflux en présence d'un agent de transfert entre phases, d'une quantité catalytique d'ion iodure et d'une base alcaline ou d'un sel basique alcalin solide sensiblement amorphe ayant une grande surface spécifique (particules d'environ 0,250 mm ou moins). Les diesters résultants peuvent être utilisés même dans les conditions stabilisantes du mélange réactionnel de l'invention comme composés intermédiaires dans les procédés de préparation de l'ibuprofène.The invention relates to a process for the preparation of an alpha -acetyl-alpha '-methylsuccinic acid diester. The product is obtained by a process which minimizes the decomposition of this diester by reacting an acetylacetate with an alpha -halopropionate in a solvent containing a nonpolar aprotic liquid at a temperature of about 50 degrees C at the reflux temperature in the presence a phase transfer agent, a catalytic amount of iodide ion and a substantially amorphous solid alkali base or alkali basic salt having a large specific surface area (particles of about 0.250 mm or less). The resulting diesters can be used even under the stabilizing conditions of the reaction mixture of the invention as intermediate compounds in the processes for the preparation of ibuprofen.

FR7807636A 1977-03-17 1978-03-16 PROCESS FOR PREPARATION OF A DIESTER OF A-ACETYL-A'-METHYLSUCCINIC ACID Withdrawn FR2383912A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US77857177A 1977-03-17 1977-03-17

Publications (1)

Publication Number Publication Date
FR2383912A1 true FR2383912A1 (en) 1978-10-13

Family

ID=25113792

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7807636A Withdrawn FR2383912A1 (en) 1977-03-17 1978-03-16 PROCESS FOR PREPARATION OF A DIESTER OF A-ACETYL-A'-METHYLSUCCINIC ACID

Country Status (4)

Country Link
JP (1) JPS53116320A (en)
DE (1) DE2806424A1 (en)
FR (1) FR2383912A1 (en)
GB (1) GB1567444A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0022440A1 (en) * 1979-06-22 1981-01-21 The Upjohn Company Process for preparing Michael addition products and for converting them to ibuprofen, an anti-inflammatory compound

Also Published As

Publication number Publication date
DE2806424A1 (en) 1978-09-21
JPS53116320A (en) 1978-10-11
GB1567444A (en) 1980-05-14

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