m-Chloroperbenzoic acid → 2,5-Dimethoxy-3,4,6-trimethylphenol

Participants

Reaction Steps

A solution of 9.4 g of m-chloroperbenzoic acid (70% purity) in 100 ml of methylene chloride was added dropwise, whilst ice-cooling, to a solution of 4.6 g of 1,4-dimethoxy-2,3,5-trimethylbenzene in 20 ml of methylene chloride, and the resulting mixture was stirred at the same temperature for 30 minutes and then at room temperature for 5 hours. At the end of this time, the reaction mixture was washed with a 5% w/v aqueous solution of sodium hydrogensulfite, with a 5% w/v aqueous solution of sodium hydrogencarbonate and with water, in that order, after which it was dried over anhydrous sodium sulfate. The solvent was then removed from the reaction mixture by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using benzene and a 50:1 by volume mixture of benzene and ethyl acetate as the eluents, to give 1.3 g of the title compound.

Provenance & Evidence