Hydrochloric Acid → HCID 178509804, compound

Participants

Reaction Conditions

Reaction Steps

4.0 g of 4-(p-cyanophenyl)cyclohexanecarboxaldehyde (prepared according to Example 1) were dissolved in 50 ml of 0.1N methanolic potassium hydroxide solution while gassing with argon in a sulphonation flask provided with a thermometer and the solution was treated portionwise at 0° C. within 20 minutes with 711 mg of sodium borohydride. The mixture was stirred at 0° C. for a further 10 minutes, neutralized with 1N hydrochloric acid and concentrated on a rotary evaporator. The residue was taken up in 200 ml of water and extracted three times with 100 ml of methylene chloride each time. The organic phases were washed twice with 100 ml of water each time, dried over magnesium sulphate and concentrated. A single crystallization of the residue (4.2 g) from 90 ml of ethyl acetate/petroleum ether (vol. 1:2) at 0° C. gave 3.27 g (77%) of p-[trans-4-(hydroxymethyl)cyclohexyl]benzonitrile as colourless crystals of melting point 109.8° C.; purity 99.4%.

Provenance & Evidence