Friedel–Crafts acylations of aromatic hydrocarbons. Part VIII. Mono- and di-acylation of mesitylene

Abstract

The Friedel–Crafts acylation of mesitylene has been studied in detail. In the acetylation, propionylation or benzoylation reactions mono- or di-ketones may be formed. Mesitoylation leads only to the monoketone. A two-stage acylation procedure is described for the synthesis of acetylbenzoylmesitylene and acetylpropionylmesitylene. Reversibility has been shown to be a factor in these acylations, especially where an aliphatic acyl group is involved. The relationship between the stereochemistry of mesityl ketones and their u.v., i.r., and ¹H n.m.r. spectra is discussed.