2-(1-HydroxyCyclohexyl)-2-(4-MethoxyPhenyl)Acetonitrile

A mixture of p-methoxyphenylacetonitrile 36 (100 g, 0.68 mol), 10% aqueous NaOH solution (100 ml, 0.25 mol) and TBAHSO4 (5 g, 0.014 mol) was stirred at room temperature for 30 minutes. A dark red colour appeared. To this was added cyclohexanone 34 (67 g, 0.680 mol) in small portions at 0 ºC, with vigorous stirring, in such a way that temperature should not rise above 10 ºC. A white solid was formed within 30 minutes to one hour. The solid was crushed and the reaction mixture was further stirred vigorously at room temperature for one more hour. The solid was filtered, washed with water till neutral to pH paper and air-dried. Crystallization from ethyl acetatepetroleum ether (500:350, v/v) gave a bright white solid (161.66 g).

White Powder

An intermediate in the synthesis of N,O-Didesmethylvenlafaxine, a metabolite of Venlafaxine