Trifluoroacetic acid catalysed Claisen rearrangement of 5-allyloxy-2-hydroxybenzoic acid and esters: an efficient synthesis of (±)-mellein
- 1 January 1982
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 19,p. 1120-1122
- https://doi.org/10.1039/c39820001120
Abstract
5-Allyloxy-2-hydroxybenzoic acid (1a) and the esters (1b–f) 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 (4a–f)via regioselective Claisen rearrangement to the 6-position of the aromatic nucleus with subsequent acid catalysed cyclisation.Keywords
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