Water → HCID 178509806, compound

Participants

Reaction Conditions

Reaction Steps

51.0 g of 4-(p-cyanophenyl)cyclohexanone were almost completely dissolved in 1.5 l of ethanol/water (vol. 4:1) and then treated within 10 minutes with 9.68 g of sodium borohydride. The mixture was stirred for a further 30 minutes and then left to stand overnight. The reaction mixture was subsequently treated cautiously with 350 ml of dilute, ice-cold hydrochloric acid (1 part of concentrated hydrochloric acid to 4 parts of water), then treated with 2 l of water and 1 l of diethyl ether and shaken. The aqueous phase was separated and extracted four times with 0.5 l of diethyl ether each time. The combined organic phases were washed with 100 ml of saturated sodium hydrogen carbonate solution and with 100 ml of saturated sodium chloride solution, dried over sodium sulphate and concentrated. The crude product, which still contained water, was dried further by dissolution in toluene and acetone and concentration. The beige, solid residue (48.9 g) was dissolved in 300 ml of hot toluene and a fine, insoluble residue was filtered off while the mixture was hot. The filtrate was cooled to -20° C. and the crystallizate obtained was filtered off under suction, washed with 50 ml of toluene/hexane (vol. 9:1) and dried. There were thus obtained 31.72 g (61.6%) of pure, light beige trans-4-(p-cyanophenyl)cyclohexanol of m.p. 119.5°-122.4° C. A further 3.21 g (6.2%) of trans-4-(p-cyanophenyl)cyclohexanol of m.p. 116.5°-122.1° C. were obtained from the mother liquor by crystallization from 60 ml of toluene at -20° C.

Provenance & Evidence