N,N-Dimethylaniline → 4-(Dimethylamino)Benzaldehyde

Participants

Reaction Conditions

Reaction Steps

83.0 g (0.54 mole) of phosphorus oxychloride was slowly added, drop by drop, to 33.3 g (0.45 mole) of dimethylformamide under cooling with ice. After stirring for a while, 55 g (0.45 mole) of dimethylaniline was added dropwise thereto and the resulting reaction mixture was stirred at 90° C. for 2 hours. The catalyst was slowly decomposed by the addition of 200 ml of ice water and the resulting mixture was made weakly alkaline by the addition of 350 g of a 20% aqueous sodium hydroxide solution. After the mixture was cooled by allowing it to stand for a while, the precipitated 4-dimethylaminobenzaldehyde was separated by filtration, washed thoroughly with water to remove any salts and impurities, and then dried at 50° C. Thus, there was obtained 59.8 g of 4-dimethylaminobenzaldehyde (in an 89% yield based on the dimethylaniline).

Provenance & Evidence