Dimethylformamide → Benzaldehyde, 4-(diphenylamino)-

Participants

Reaction Conditions

Reaction Steps

46 g of phosphoryl trichloride (POCl3) was added dropwise to 22 g of N,N-dimethylformamide while stirring on a ice bath, and the stirring was continued for about 1 hour to produce a sirupy Vilsmeier reagent. To this reagent, a solution containing 50 g of N,N,N-triphenylamine in 200 ml of N,N-dimethylformamide was added while maintaining on the ice bath. After continued the stirring for about 1 hour, the temperature of the bath was raised to about 90° C., and the mixture was stirred for 2 additional hours. After the reaction, the mixture was cooled to room temperature and poured into ice. The resulted aqueous solution was neutralized with alkali to form a yellow precipitate. After it was separated by filtration and dried, it was recrystallized with ethyl alcohol to obtain 43 g of p-(N,N-diphenylamino)benzaldehyde.

Provenance & Evidence