Access to "Friedel-Crafts-Restricted" tert-Alkyl Aromatics by Activation/Methylation of Tertiary Benzylic Alcohols

Joshua A. Hartsel, Derek T. Craft, Qiao-Hong Chen, Ming Ma and Paul R. Carlier *

*Department of Chemistry, Virginia Tech, Blacksburg, Virginia 24061, United States, Email: pcarliervt.edu

J. A. Hartsel, D. T. Craft, Q.-H. Chen, M. Ma, P. R. Carlier, J. Org. Chem., 2012, 77, 3127-3133.

DOI: 10.1021/jo202371c

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Abstract

Activation of tertiary benzylic alcohols with SOCl₂ or concentrated HCl followed by treatment with trimethylaluminum allows the synthesis of m-tert-alkylbenzenes in good yields. 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.

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Key Words

Benzylation

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ID: J42-Y2012-0920