Issue 19, 1982

Trifluoroacetic acid catalysed Claisen rearrangement of 5-allyloxy-2-hydroxybenzoic acid and esters: an efficient synthesis of (±)-mellein

Abstract

5-Allyloxy-2-hydroxybenzoic acid (1a) and the esters (1bf) in refluxing trifluoroacetic acid are smoothly converted into 3,4-dihydro-5,8-dihydroxy-3-methylisocoumarin (3) and the corresponding 4-alkoxycarbonyl 2,3-dihydro-5-hydroxy-2-methylbenzofurans (4af)via regioselective Claisen rearrangement to the 6-position of the aromatic nucleus with subsequent acid catalysed cyclisation.

Article information

Article type
Paper

J. Chem. Soc., Chem. Commun., 1982, 1120-1122

Trifluoroacetic acid catalysed Claisen rearrangement of 5-allyloxy-2-hydroxybenzoic acid and esters: an efficient synthesis of (±)-mellein

L. M. Harwood, J. Chem. Soc., Chem. Commun., 1982, 1120 DOI: 10.1039/C39820001120

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