Ammonia → HCID 178444572, compound

Participants

Reaction Steps

1.63 g of 4-(1E-pentenyl)cyclohexanone were dissolved in 8 ml of diethyl ether and 14 ml of ethanol. The solution was subsequently treated dropwise with about 70 ml of ammonia and the mixture was treated portionwise with lithium wire until the colour of the reaction mixture remained constant for 1.5 hours (about 1.3 g of lithium). Thereafter, the ammonia was evaporated off and the mixture was made acid with ammonium chloride and hydrochloric acid and left to stand for 3 days. The reaction mixture was then partitioned in diethyl ether/water and the aqueous phases were back-extracted with diethyl ether. The organic phases were dried over magnesium sulphate, filtered and freed from solvent on a rotary evaporator. Low-pressure chromatography of the residual, yellow oil on silica gel with ethyl acetate/petroleum ether (vol. 10:90) gave 1.47 g (89.1%) of trans-4-(1E-pentenyl)cyclohexanol as a light yellow, viscous oil.

Provenance & Evidence