Phosphorus oxychloride → N,N-dioctadecylaminobenzaldehyde

Participants

Reaction Conditions

Reaction Steps

Phosphorus oxychloride (15.3 g, 0.1 mole) was added dropwise with stirring, at 5° C., under nitrogen, to N,N-dimethylformamide (DMF, 50 mL). The resulting orange solution was stirred for 2 hours, then 42 g (0.08 mole) of N,N-dioctadecylaniline was added all at once. The reaction mixture was heated in a water bath to 90° C., and stirring was continued for 4 hours. The hot solution was poured over 200 g of crushed ice and naturalized to pH 6 by a slow addition of solid sodium acetate with vigorous stirring. The greenish-tint crystalline precipitate was filtered by suction, washed with water on the filter and air dried. The light green product was recrystallized from isopropanol to yield 46.5 g (93%) of pale-green crystals mp 65°-66° C.

Provenance & Evidence