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Synthesis 1989; 1989(1): 25-28
DOI: 10.1055/s-1989-27134
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Titanium Tetrachloride Induced Fries Rearrangement: A New Route to Disubstituted 2′- Hydroxypropiophenones

Robert Martin* , Pierre Demerseman
  • *Service de Chimie de l'Institut Curie, E. R. no 213 CNRS, 26 rue d'Ulm, F-75231 Paris Cedex 05, France
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Publication Date:
27 September 2002 (online)

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Fries rearrangement of some dialkylphenyl propionates with titanium tetrachloride proves to be a convenient route to hindered dialkyl 2′-hydroxypropiophenones. The sequential use of soft titanium tetrachloride to perform the Fries rearrangement followed by hard aluminum chloride to achieve the elimination of a protecting tert-butyl group allows the synthesis of some previously unknown 3′,6′- and 5′,6′-dialkyl-2-hydroxypropiophenones.