Acetonin → p-Toluenesulfonic acid

Participants

Reaction Steps

A solution of 19 g. of p-toluenesulfonic acid monohydrate in 40 ml. of acetone was added dropwise to a solution of 15.5 g. of acetonine in 30 ml. of acetone under cooling to 0°-5°C. and under stirring, to form p-toluenesulfonic acid salt of acetonine. The mixture was stirred at 25°C. for 10 hours to effect the reaction and cooled with ice. Crystals thus formed were filtered out and washed with cold acetone and the washing was combined with the filtrate and concentrated. The concentration residue was extracted with benzene. The benzene solution was washed with 20% aqueous sodium hydrogencarbonate solution and dried with anhydrous potassium carbonate. Benzene was then distilled out. The residue was subjected to distillation under reduced pressure to obtain 13.5 g. of triacetonamine in the form of pale yellow liquid boiling at 79°C./6 mmHg. Yield, 86.7%.

Provenance & Evidence