Selective para metalation of unprotected 3-methoxy and 3,5-dimethoxy benzoic acids with n-butyl lithium–potassium tert-butoxide (LIC–KOR): synthesis of 3,5-dimethoxy-4-methyl benzoic acid

Sinha, Surajit and Mandal, Bhubaneswar and Chandrasekaran, Srinivasan (2000) Selective para metalation of unprotected 3-methoxy and 3,5-dimethoxy benzoic acids with n-butyl lithium–potassium tert-butoxide (LIC–KOR): synthesis of 3,5-dimethoxy-4-methyl benzoic acid. In: Tetrahedron Letters, 41 (17). pp. 3157-3160.

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Abstract

The potassium salt of 3-methoxy and 3,5-dimethoxy benzoic acids undergoes deprotonation at the position para to the carboxylate group selectively when treated with LIC–KOR in THF at -$78^oC$ and it has been extended to the synthesis of 3,5-dimethoxy-4-methyl benzoic acid.

Item Type:	Journal Article
Publication:	Tetrahedron Letters
Publisher:	Elsevier B.V.
Additional Information:	Copyright of this article belongs to Elsevier.
Keywords:	alkylation;carboxylic acids;metalation.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	30 Jul 2008
Last Modified:	19 Sep 2010 04:48
URI:	http://eprints.iisc.ac.in/id/eprint/15359

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