4-Hydroxy-α-(1-hydroxycyclohexyl)benzeneacetonitrile synthesis

Yield:918344-20-4 66%

Reaction Conditions:

Stage #1: 4-cyanomethylphenol;cyclohexanonewith potassium tert-butylate at 20; for 1.5 h;
Stage #2: with hydrogenchloride in water;ethyl acetate; pH=3 - 4;Product distribution / selectivity;

Steps:

1

8.4 g of potassium tert-butylate are added at room temperature to a solution of 10 g of 4-hydroxybenzyl cyanide in 22.1 g of cyclohexanone. The mixture is stirred for 1.5 hours (h) at room temperature and 100 ml of water and 100 ml of ethyl acetate are then added. The mixture is brought to pH 3-4 with hydrochloric acid and the organic phase is separated off, dried with sodium sulfate and concentrated on a rotary evaporator. Heptane is added to the residue, the mixture is partially concentrated again and a white solid precipitates out. The solid is filtered off, washed with heptane and dried under vacuum to give 11.5 g of 1-[cyano(4-hydroxyphenyl)methyl]cyclohexanol (66% of theory).

References:

US2007/21627,2007,A1 Location in patent:Page/Page column 2