Toluene → 2-Acetoxy-6-methoxytoluene

Participants

Reaction Conditions

Reaction Steps

A solution of 5.01 g (30.0 mmol) of 2-acetoxy-6-hydroxytoluene in 50 mL of acetonitrile was added with 12.44 g (90.0 mmol) of potassium carbonate and 12.77 g (90.0 mmol) of methyl iodide and heated and stirred on a 90° C. oil bath for 96 minutes. The reaction mixture which had been allowed to stand at room temperature for about 3 hours was added to a mixture of 100 mL of toluene and 100 mL of water stirred on an ice-water bath, and after stirred for two minutes, transferred to a separatory funnel and then settled. The aqueous layer was separated and discarded and after the organic layer was washed with 20 mL of 1 N aqueous sodium hydroxide and 20 mL of water three times, and the solvent was evaporated to obtain 4.69 g of title compound.

Provenance & Evidence