Potassium Hydroxide → HCID 178509752, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 21.9 g of 4-[2-(p-cyanophenyl)ethyl]cyclohexanecarboxaldehyde (trans/cis=4:1) and 167 ml of 0.1N methanolic potassium hydroxide solution was cooled to 0° C. while stirring and gassing with nitrogen, treated portionwise within 20 minutes with 3.5 g of sodium borohydride and thereafter stirred for a further 30 minutes at 0° C. Subsequently, the grey suspension was poured cautiously on to 420 ml of ice-water and extracted three times with 300 ml of methylene chloride each time. The organic phases were washed twice with 150 ml of water each time, dried over sodium sulphate and concentrated in vacuo at 50° C. The colourless, crystalline residue of p-[2-(4-hydroxymethylcyclohexyl)ethyl]benzonitrile (22.0 g, trans/cis=89.4:10.6) was dissolved in 100 ml of ethyl acetate while warming, treated with 100 ml of hexane and cooled to 15° C. while stirring, whereby crystallization occurred. The mixture was then treated with a further 300 ml of hexane while stirring, suction filtered (rinsing with hexane) and the precipitate was dried in vacuo at 50° C. The mother liquor was worked-up in an analogous manner and then the two crystallizates (a total of 17.3 g) were recrystallized from ethyl acetate/hexane. There were obtained 16.2 g (74%) of pure p-[2-(trans-4-hydroxymethylcyclohexyl)ethyl]benzonitrile as colourless crystals with m.p. 119.2°-121.1° C.

Provenance & Evidence