Pyridine → Acetophenone

Participants

Reaction Conditions

Reaction Steps

4.7 g (38.4 mmol) of rac.-1-phenylethanol and 3.18 g (40.2 mmol) of pyridine were dissolved in 60 ml of ethyl acetate under an inert gas in a 200 ml sulphonation flask. The mixture was cooled to 0° C. while stirring and treated with 60 mg (0.28 mmol) of TEMPO derivative E. Thereafter, a solution of 3.6 g (15.5 mmol) of trichloroisocyanuric acid in 38 ml of ethyl acetate was dosed in within 1 hour at a temperature of 0°-3° C. The reaction mixture was stirred at 0°-3° C. for a further 1 hour. Thereafter, the reaction had finished. The white precipitate was filtered off and the filtrate was treated with a solution of sodium pyrosulphite in order to reduce the excess trichloroisocyanuric acid. The filtrate was washed with sodium bicarbonate solution and with sodium chloride solution. 4.7 g (102%) of acetophenone were obtained as the crude product, GC content: 99.8%. Distillation of the crude product gave 3.19 g (69%) of acetophenone, GC content: 99.9% (area percent).

Provenance & Evidence