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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Reactions of Methyl threo-2-Acetoxy-3-chloro-3-(4-methoxyphenyl)propanoate and Methyl cis-2,3-Epoxy-3-(4-methoxyphenyl)propanoate With 3,5-Dimethoxyphenol: Potential Routes to Flavan-3-ols

RFC Brown, WR Jackson, TD Mccarthy and GD Fallon

Australian Journal of Chemistry 45(11) 1833 - 1843
Published: 1992

Abstract

Attempted syntheses of flavan-3-ols by reaction of either methyl threo-2-acetoxy-3-chloro-3-(4-methoxypheny1)propanoate (3) or methyl cis-2,3-epoxy-3-(4-methoxypheny1)propanoate (14) with 3,5-dimethoxyphenol failed to give the required aryl ethers. Products usually were derived from C-alkylation of the electron-rich phenol although reaction of the chloro acetate (3) with the phenoxide ion gave the furanone (5). The single-crystal X-ray structures of methyl 4-hydroxy-3-(4-methoxyphenyl)-2-(4-methoxyphenylmethyl)-5-oxo-2,5-dihydrofuran-2-carboxylate and cis-3-hydroxy-5,7-dimethoxy-4(4-methoxyphenyl)-3,4dihydr-2H-1-benzopyran-2-one have been determined.

https://doi.org/10.1071/CH9921833

© CSIRO 1992

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