tert-Butanol → tert-Butyl (4-methylphenyl)acetate

Participants

Reaction Conditions

Reaction Steps

450 g (3 mol) of 4-methylphenyl-acetic acid (Aldrich), 1.13 l (12 mol) of tert-butanol and 90 g (0.74 mol) of 4-(N,N-dimethylamino)pyridine are dissolved in 2 l of methylene chloride. After addition of 680 g (3.3 mol) of dicyclohexylcarbodiimide, dissolved in 400 ml of methylene chloride, the mixture is stirred at 25° C. for 20 hours, the urea which has precipitated out is filtered off with suction and washed with 200 ml of methylene chloride and the organic phase is washed in each case twice with 500 ml of 2M hydrochloric acid and water. The organic phase is concentrated and distilled. Yield: 408 g (66% of theory) Boiling point: 73°-78° C./0.2 mm

Provenance & Evidence