Issue 0, 1979

The reaction of hydroquinone and monosubstituted hydroquinones with dimethyl chloromalonate

Abstract

Hydroquinone and monosubstituted hydroquinones free from –I,–M groups react with dimethyl chloromalonate in methanolic sodium methoxide solution to give 2-oxido-benzo[b]furan derivatives (1). The mechanism of this base catalysed C-alkylation is interpreted in terms of initial mono-O-alkylation followed by fragmentation and 1,4-addition of dimethyl sodiomalonate to the nascent 1,4-benzoquinone so formed. The procedure furnishes, in moderate to high yield, products which cannot be prepared readily by direct nucleophilic addition to 1,4-benzoquinones.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1979, 2382-2386

The reaction of hydroquinone and monosubstituted hydroquinones with dimethyl chloromalonate

A. H. Renfrew, S. B. Bostock and C. M. Ecob, J. Chem. Soc., Perkin Trans. 1, 1979, 2382 DOI: 10.1039/P19790002382

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