4-Hydroxybenzyl Alcohol → 4-Hydroxybenzyl cyanide

Temperature

40 °C

n-Propyl formate (264 g.) and granular sodium cyanide (150 g.) were added successively to a stirred suspension of p-hydroxybenzyl alcohol (8310 g.) in N,N-dimethylformamide (148 g.) and the mixture was heated at 67°-68° C. for 1 hour, cooled to 40° C. and poured into water (588 ml.). The mixture was cooled to 20°-25° C., the pH of the mixture was adjusted from 9.5 to 4.0 with 98% formic acid (270 ml.), and the mixture was extracted three times with isobutyl methyl ketone (677 ml, 196 ml. and 196 ml. successively). Each extract was washed twice with water (196 ml. each time) and the combined extracts were dried by azeotropic distillation under reduced pressure at 60°-70° C. There was thus obtained p-hydroxybenzyl cyanide (319 g., 96% yield).

1. temperaturethe mixture was heated at 67°-68° C. for 1 hour
2. temperatureThe mixture was cooled to 20°-25° C.
3. extractionthe mixture was extracted three times with isobutyl methyl ketone (677 ml, 196 ml
4. washEach extract was washed twice with water (196 ml
5. customeach time) and the combined extracts were dried by azeotropic distillation under reduced pressure at 60°-70° C

ORD record

ord-59c82bb351ee49e6931815b153d15174

Source dataset

uspto-grants-1982_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04317781