Synthesis of α-hydroxyacetophenones

J Org Chem. 2012 Jun 1;77(11):5144-8. doi: 10.1021/jo3005556. Epub 2012 May 22.

Abstract

A general method for the preparation of α-hydroxyacetophenones is presented. Functionalized arylmagnesium species are transmetalated to the corresponding arylzinc intermediates, which undergo Cu(I)-catalyzed reaction with acetoxyacetyl chloride. Acidic hydrolysis of the acetate group releases the target α-hydroxyacetophenones with minimal production of undesired polymeric degradates that are often observed under alternative conditions.

MeSH terms

  • Acetates / chemistry
  • Acetophenones / chemical synthesis*
  • Acetophenones / chemistry*
  • Catalysis
  • Hydrolysis
  • Molecular Structure
  • Organometallic Compounds / chemistry
  • Stereoisomerism

Substances

  • Acetates
  • Acetophenones
  • Organometallic Compounds