Substituent Effects in the Bf 3 -Mediated Acylation of Phenols with Cinnamic Acids

Author: Daskiewicz Jean-Baptiste   Barron Denis  

Publisher: Taylor & Francis Ltd

ISSN: 1478-6419

Source: Natural Product Research, Vol.17, Iss.5, 2003-10, pp. : 347-350

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Abstract

2′,4′-Dihydroxy-4-nitrochalcone was obtained by BF3 etherate acylation of resorcinol with 4-nitrocinnamic acid. Instead, when p-methoxycinnamic or p-coumaric acids were used, the main product of the reaction was the coumarin umbelliferone, while no chalcone was present. These effects are commented in relation to the nature of the substituent present on the cinnamic acid moiety.