M. Yodo, H. Harada
Sep 25, 1989
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0
Influential Citations
4
Citations
Journal
Chemical & Pharmaceutical Bulletin
Abstract
A method for synthesizing methyl 2,3-dihydro-2-benzofurancarboxylates from o-allylphenols is described. The reaction of 6-allyl-2,3-dichlorophenol, with benzenesulfenyl chloride (PhSCl) in acetonitrile gave a mixture of PhSCl-adducts, which was heated in aqueous acetonitrile then with sodium bicarbonate to obtain 6,7-dichloro-2-(phenylthiomethyl)-2,3-dihydrobenzofuran. α-Dichlorination of the phenylthiomethyl group of 6 and subsequent mrethanolysis gave the methyl ester in high yield. The generality of this synthetic method was examined by the conversion of o-allylphenols having various substituents on the benzene ring into the corresponding methyl esters