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Synthesis 2014; 46(02): 263-268
DOI: 10.1055/s-0033-1340285
paper
© Georg Thieme Verlag Stuttgart · New York

Methyl Salicylate as a Selective Methylation Agent for the Esterification of Carboxylic Acids

Si Chen
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. of China   Fax: +86(28)85462021   eMail: luomm@scu.edu.cn
,
Lei Jia
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. of China   Fax: +86(28)85462021   eMail: luomm@scu.edu.cn
,
Xiaonan Li
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. of China   Fax: +86(28)85462021   eMail: luomm@scu.edu.cn
,
Meiming Luo*
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. of China   Fax: +86(28)85462021   eMail: luomm@scu.edu.cn
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Publikationsverlauf

Received: 16. August 2013

Accepted after revision: 28. Oktober 2013

Publikationsdatum:
26. November 2013 (online)

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Abstract

Methyl salicylate is a selective and inexpensive methylating agent for the esterification of carboxylic acids with a wide range of functional group tolerance. The intramolecular hydrogen bonds between the carboxylate and hydroxyl groups in methyl salicylate are essential for the transformation. Allyl, benzyl, methallyl, and propargyl salicylates can also be used as alkylating agents for the preparation of the corresponding alkyl carboxylates.

Key words

carboxylic acid - esterification - esters - alkylation - methyl salicylate

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    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
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