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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 10, 1980 - Issue 1
145
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Original Articles

A Novel Ring Opening of Coumarins

, , , &
Pages 37-42 | Received 31 Jul 1979, Published online: 03 Jan 2007
 

Abstract

During our work on the synthesis of some Piper amides we were encountered with a problem of synthesising o-methoxy cinnamic acids. Besides the conventional method of preparing such compounds from substituted salisaldehyde derivatives, the opening of coumarin ring by Rao et al1 using dimethyl sulphate and sodium hydroxide is known to give the mixture of cis and trans o-methoxy cinnamic acid with the predominance of trans form (∼ 80%). Use of aq. Sodium hydroxide thus seems to be of little help in the formation of less stable cis isomer. Therefore, it was decided to make

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