Standard Article

The Fries Reaction

  1. A. H. Blatt

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or001.11

Organic Reactions

Organic Reactions

How to Cite

Blatt, A. H. 2011. The Fries Reaction. Organic Reactions. 1:11:342–369.

Author Information

  1. Queens College

Publication History

  1. Published Online: 15 MAR 2011

Abstract

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