Dimethylformamide → Benzaldehyde, 4-(diphenylamino)-

Participants

Reaction Conditions

Reaction Steps

A Vilsmeier's reagent was prepared by adding dropwise phosphoryl trichloride (POCl3) (46 g) to N,N-dimethylformamide (22 g) with stirring in an ice bath. Thereto there was added a solution (200 ml) of N,N,N-triphenylamine (50 g) in N,N-dimethylformamide while continuing cooling in the ice bath. The stirring was continued for about one hour, and then the bath temperature was raised to about 90° C. While maintaining that temperature, the stirring was continued further for two hours. At the conclusion of the reaction the reaction system was cooled to room temperature, and then the reaction product was poured into ice water. The thus obtained aqueous solution was neutralized with an alkali to separate out a yellow precipitate. The precipitate was filtered off, dried and then recrystallized from ethyl alcohol. Thus, p-(N,N-diphenylamino)benzaldehyde (43 g) was obtained.

Provenance & Evidence