Dimethylformamide → Methyl 2,6-dimethylbenzoate

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.) solution of 2,6-dimethylbenzoic acid (20.2 g, 134 mmol) in dichloromethane (200 mL) is added DMF (1 mL) followed by oxalyl chloride (14 mL, 162 mmol). On completion of addition, the cold bath is removed and stirring continued for 3 h. The resulting solution is concentrated under vacuum and the residue added slowly to a cooled (0° C.) solution comprising methanol (200 mL) and triethylamine (40 mL). On completion of addition, the reaction mixture is stirred for 30 min. then poured into hydrochloric acid solution (400 mL, 2N) which is then extracted with ether. The ether extract is washed with hydrochloric acid solution (1N), sodium bicarbonate solution and brine then dried over MgSO4 and concentrated to give the title compound which is used without further purification. MS (EI) 164 (M)+.

Provenance & Evidence