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 degrees C and it has been extended to the synthesis of 3,5-dimethoxy-4-methyl benzoic acid. (C) 2000 Elsevier Science Ltd. All rights reserved.

Item Type:	Journal Article
Additional Information:	Copyright of this article belongs to Elsevier science.
Keywords:	alkylation;carboxylic acids;metalation
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	16 Aug 2010 11:17
Last Modified:	19 Sep 2010 06:14
URI:	http://eprints.iisc.ernet.in/id/eprint/31275

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