Trichloroisocyanuric Acid → 4-Nitrobenzaldehyde

Participants

Reaction Steps

5 g (32.6 mmol) of 4-nitrobenzylalcohol, 2.7 g (32.9 mmol) of sodium acetate and 10 mg (0.06 mmol) of TEMPO were suspended in 40 ml of methylene chloride in a 100 ml sulphonation flask and the suspension was cooled to (-8)-(-10)° C. while stirring. A solution of 3.03 g (13.0 mmol) of trichloroisocyanuric acid in 20 ml of acetone was dosed in within 1 hour, whereupon the mixture was held at (-5)° C. for 1 hour. Thereafter, the reaction had finished. The white precipitate was filtered off and the filtrate was washed with sodium bicarbonate solution and with sodium chloride solution. The organic phase was concentrated and the residue was recrystallized from diisopropyl ether. There were obtained 4.62 g (94%) of 4-nitrobenzaldehyde, GC content: (97.7%) (area percent).

Provenance & Evidence