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

Roger F.C. Brown, W. Roy Jackson, Tom D. McCarthy, Gary D. Fallon

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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.

Original languageEnglish
Pages (from-to)1833-1843
Number of pages11
JournalAustralian Journal of Chemistry
Issue number11
Publication statusPublished - 1992

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