Trimethylcatecholdiester und Verfahren zu seiner Herstellung

Trimethylcatechol diester and a method for producing the same

Diester du triméthylcatéchol et son procédé de préparation

Abstract

This method provides a novel trimethylcatechol diester, i.e. 3,4,5-trimethylcatechol diester, at a high yield by reacting 2,6,6-trimethylcyclohexe-2-en-1,4-dione with an acylating agent in the presence of an acid catalyst. The acylating agent includes a C 2-4 carboxylic acid anhydride (e.g. acetic anhydride) and a C 2-4 carboxylic acid halide (e.g. acetyl chloride). The catalyst includes a protonic acid and a Lewis acid. Use of a polar solvent (e.g. halogenated hydrocarbon), as the reaction catalyst, results in an enhanced efficiency in the production of the object compound.

Claims

Description

Topics

Download Full PDF Version (Non-Commercial Use)

Patent Citations (2)

    Publication numberPublication dateAssigneeTitle
    DE-2149159-A1April 06, 1972Eastman Kodak CoTrimethylhydroquinone prepn - from 2,6,6-trimethyl-2-cyclohexene-1,4-
    GB-1316739-AMay 16, 1973Texaco Development CorpPreparation of acetates of monohydric and dihydric phenols

NO-Patent Citations (1)

    Title
    ARYEH A. FRIMER ET AL. : "Electronic and Steric Effects in the Dienone-Phenol Rearrangement of 2-Hydroxy- and 2-Alkoxycyclohexa-2,5-dien-1-ones" JOURNAL OF ORGANIC CHEMISTRY., vol. 59, no. 7, 8 April 1994, EASTON US, pages 1831-1834, XP002057360

Cited By (12)

    Publication numberPublication dateAssigneeTitle
    EP-0916642-A1May 19, 1999Daicel Chemical Industries, Ltd.Hydrochinondiester sowie Verfahren zu deren Herstellung
    EP-1008584-A1June 14, 2000Degussa AktiengesellschaftProcédé de préparation de diesters de la triméthylhydrochinone et de la triméthylhydrochinone
    EP-1028103-A1August 16, 2000Degussa-Hüls AktiengesellschaftProcédé pour la préparation de diesters de 2,3,5-trimethylhydroquinone
    US-5969176-AOctober 19, 1999Degussa-Huls AgProcess for the production of trimethylhydroquinone diesters and of trimethylhydroquinone
    US-6350897-B2February 26, 2002Degussa AgProcess for preparing trimethylhydroquinone diacetate and trimethylhydroquinone
    US-6369263-B1April 09, 2002Daicel Chemical Industries, Ltd.Process for producing hydroquinone diester derivative
    US-6417409-B1July 09, 2002Degussa-Huls AgProcess for the production of 2,3,5-trimethylhydroquinone diesters
    US-6444841-B2September 03, 2002Daicel Chemical Industries, Ltd.Hydroquinone diester derivatives and the method for producing the same
    US-8313733-B2November 20, 2012Colgate-Palmolive CompanyAntibacterial 5,5′-disubstituted 3,3′ dialkoxy-2,2′-dihydroxy-1,1′-biphenyl
    US-8425881-B2April 23, 2013Colgate-Palmolive CompanyAntibacterial 3′,5-disubstituted 2,4′-dihydroxybiphenyl compounds, derivatives and related methods
    WO-0040540-A1July 13, 2000Daicel Chemical Industries, Ltd.Process for producing hydroquinone diester derivative
    WO-2009045951-A1April 09, 2009Colgate-Palmolive CompanyPyrocatéchols antibactériens et procédés relatifs