Acetyl chloride → N-acetyl-o-toluidine

Participants

Reaction Conditions

Reaction Steps

Ortho toluidine (0.75 mol, 80 grams) was taken in a 1 L round bottom flask equipped with a liquid addition funnel and a guard tube. Triethylamine (1.13 mmol, 113.77 grams) was added to it in one lot. Above mixture was cooled to 0-5° C. and acetyl chloride (1.13 mmol, 88.7 grams) was added drop wise by maintaining the temperature below 10° C. After addition of acetyl chloride, cooling was removed and the reaction mass was stirred at 25-28° C. for a period of 3 hours. After completion of the reaction, the reaction mixture was poured onto 500 grams of ice-water and extracted with dichloromethane (2×300 mL). The combined dichloromethane extracts were then washed with water, brine and dried over anhydrous magnesium sulfate. The volatiles were removed under the reduced pressure to obtain 113.6 grams of solid product.

Provenance & Evidence