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 ; Mandal, Bhubaneswar ; 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 Tetrahedron Letters, 41 (17). pp. 3157-3160. ISSN 0040-4039

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...

Related URL: http://dx.doi.org/10.1016/S0040-4039(00)00320-8

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°C and it has been extended to the synthesis of 3,5-dimethoxy-4-methyl benzoic acid.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Alkylation; Carboxylic Acids; Metalation
ID Code:7205
Deposited On:25 Oct 2010 12:11
Last Modified:01 Feb 2011 11:15

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