Access to "Friedel-Crafts-restricted" tert-alkyl aromatics by activation/methylation of tertiary benzylic alcohols

J Org Chem. 2012 Apr 6;77(7):3127-33. doi: 10.1021/jo202371c. Epub 2012 Mar 16.

Abstract

Herein we describe a two-step protocol to prepare m-tert-alkylbenzenes. The appropriate tertiary benzylic alcohols are activated with SOCl(2) or concentrated HCl and then treated with trimethylaluminum, affording the desired products in 68-97% yields (22 examples). This reaction sequence is successful in the presence of a variety of functional groups, including acid-sensitive and Lewis-basic groups. In addition to t-Bu groups, 1,1-dimethylpropyl and 1-ethyl-1-methylpropyl groups can also be installed using this method.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Alcohols / chemistry*
  • Benzene Derivatives / chemistry*
  • Benzyl Compounds / chemistry*
  • Catalysis
  • Methylation
  • Molecular Structure
  • Stereoisomerism

Substances

  • Alcohols
  • Benzene Derivatives
  • Benzyl Compounds