p-[4-(Methoxymethylene)cyclohexyl]benzonitrile → 4-(4-Formylcyclohexyl)benzonitrile

Participants

Reaction Steps

The resulting oil (11.0 g) of p-[4-(methoxymethylidene)cyclohexyl]benzonitrile was heated to boiling for 1 hour in a mixture of 200 ml of tetrahydrofuran and 50 ml of 2N hydrochloric acid. The mixture was subsequently poured on to 500 ml of ice/water and extracted three times with 200 ml of diethyl ether each time. The organic phases were washed neutral with water, dried over sodium sulphate and concentrated, thereby obtaining 10.0 g of colourless and in part solid 4-(p-cyanophenyl)cyclohexanecarboxaldehyde (cis/trans ratio about 1:3).

Provenance & Evidence