Oxidation of mesitylene by hydrogen peroxide in AcOH-Ac2O-H2SO4

By the oxidation of raesitylene by hydrogen peroxide in AcOH-Ac₂O-H₂SO₄ one can obtain mesitol (2,4,6-trimethylphenol) (with a selectivity of 57–69% at a mesitylene conversion of 22–16% and the acetate of mesitol with a selectivity of 72–85% at 25–22% conversion. The peroxide responsible for the oxidation of mesitylene in this system is in the form of peracetic acid, formedin situ. Over the concentration range studied, the reaction is first order in AcOOH, mesitylene, and H₂SO₄. Hydroxylation of mesitylene by AcOOH proceeds by an electrophilic substitution mechanism, the limiting step being the formation of the -complex.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2716–2721, December, 1990.The authors express their thanks to L. V. Efremova, G. M. Maksimov, and V. D. Chinakov for their assistance in this work.