反应详情

Under a nitrogen atmosphere, 4-acetoxycinnamic acid (150 g) and N,N-dimethylformamide (5 ml) were suspended in chloroform (800 ml) and thereto was added dropwise thionyl chloride (104 g) over a period of about 30 minutes. After completion of the addition, the reaction mixture was reflexed with heating for 1 hour to prepare the corresponding acid chloride. The reaction mixture was cooled to room temperature and thereto was added dropwise a solution of octadecylamine (196 g) and triethylamine (81 g) in chloroform (50 ml) over a period of about 30 minutes, followed by refluxing with heating for 3 hours. The reaction mixture was cooled to room temperature to precipitate a white crystal, which was filtered off under reduced pressure and dried to obtain N-octadecyl-p-acetoxycinnamamide (258 g). Yield 78%. This was suspended in 1,4-dioxane (1200 ml) and thereto was added aqueous KOH solution 50%; 127 g) and the reaction was allowed to proceed at 40°-45° C. for 24 hours. After completion of the reaction, the reaction mixture was cooled to room temperature to precipitate a white crystal, which was filtered off under reduced pressure. This crystal was washed with distilled water and recrystallized from methanol to obtain the desired product (211 g). Yield 90%; m.p. 114° C.

1. additionAfter completion of the addition
2. temperaturewith heating for 1 hour
3. temperatureby refluxing
4. temperaturewith heating for 3 hours
5. temperatureThe reaction mixture was cooled to room temperature
6. customto precipitate a white crystal, which
7. filtrationwas filtered off under reduced pressure
8. customdried