Triethylamine → 2-Chloro-4-methylphenyl 2,2-dimethylpropanoate

Participants

Reaction Steps

To a mixture of 100 g of 2-chloro-4-methylphenol, 92.3 g of triethylamine and 1 liter of anhydrous tetrahydrofuran was added dropwise 93.0 g of pivaloyl chloride at 5° to 10° C. under stirring over 1 hour. Then, after stirring at the same temperature for 3 hours, the reaction mixture was poured into ice water, which was extracted with diethyl ether. The organic layer was washed with 3% aqueous hydrochloric acid and then water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting oil was distilled under reduced pressure, which afforded 155.3 g of 2-chloro4-methylphenyl 2,2-dimethylpropanoate as a colorless clear liquid. Yield, 97.7%.

Provenance & Evidence