The Fries Reaction

The Fries reaction consists in the conversion of an ester of a phenol to an ortho- or para-hydroxyketone, or a mixture of both, by treatment with aluminum chloride. Three different mechanisms for the fries rearrangement have received serious consideration.: the ester is assumed to react with aluminum chloride to give an acid chloride and a phenoxyaluminum chloride which combine to form a derivative of the hydroxyketone; one molecule of the phenyl ester is acylated by another molecule; the Fries reaction is considered ti be a true intramolecular rearrangement in which the acyl group shifts directly from the oxygen atom to the carbon atom of the ring. Keywords: Fries reaction; temperature; solvents; acyl radical; phenoxy group; ester-reagent ration; experimental conditions

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