Fries Rearrangement of o-Carboxy-β-substituted Phenolic Esters

Fries rearrangements of 5-methyl-, 5-bromo-, and 5-chloro-2-acetoxytenzoic acids have teen effected, affuirding the corresponding 5-substituted-2-hydroxyacephenone-3-carboxylic acids. Fries rearrangement of the corresponding 2-propionyloxy analogues have also been studied, the reaction being successful only With 5-methyl-2-propionyloxybenzoic acid. The hydroxyketones thus formed have also been synthesised by the Friedel-Crafts acylation of the appropriate 5-substituted-2-hydroxybenzoic acids