Water → HCID 21480569, compound

Participants

Reaction Steps

4-(4-Methoxybenzyl)cyclohexanone (112 g) (prepared as described in Example 1 (a)) pyrrolidine (100 g), and p-toluene sulphonic acid (0.3 g) were dissolved in toluene (1.56) and heated to reflux under argon with Dean-Stark water separation. When water ceased to separate (ca 2.5 hours) the remaining pyrrolidine and solvent were evaporated off and the residue dissolved in absolute ethanol (1 litre). The product was treated with acrylonitrile (27.2 g) in ethanol (30 ml). After 2 hours at reflux the reaction was left to cool and then concentrated in vacuo. The residue was treated with water (1 litre) and acetic acid (200 ml). After stirring for 2 hours the mixture was extracted into diethyl ether and the organic phase dried (Na2SO4) and concentrated to yield 2-(2-cyanoethyl)-4-(4-methoxyphenyl)cyclohexanone as an oil (140 g).

Provenance & Evidence