Oxidation of Mesitylene by Hydrogen Peroxide in AcOH-Ac2O-H2SO4
Russian Chemical Bulletin
, E-ISSN: 1573-9171
Institute of Catalysis, Siberian Branch of the Academy of Sciences of the USSR
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 σ-complex.