Hydrochloric Acid → (1-Hydroxycyclohexyl)(4-methoxyphenyl)acetonitrile

Participants

Reaction Steps

Lithium diisopropylamide was made from 1.6M butyl lithium in hexane (325 ml), diisopropylamine (73 ml) and toluene (300 ml) under an inert atmosphere of nitrogen. A solution of p-methoxyphenylacetonitrile (76.5 g) in toluene (75 ml) was added to the solution under nitrogen over 15 minutes whilst the internal temperature was maintained below 10° C. After a half hour a solution of cyclohexanone (46 g) in toluene (50 ml) was added over 15 minutes to the reaction mixture under nitrogen whilst the internal temperature was maintained below 10° C. After a further half hour the mixture was blown over onto an ice-cold mixture of 12N hydrochloric acid (100 ml) and water (1l). The crystalline material was filtered off and then taken up into dichloromethane. The solution was washed with water and dried. The solvent was replaced with di-isopropyl ether by distillation. After cooling, the product was filtered and dried in vacuo to yield 91 g (79% yield ) of the title compound.

Provenance & Evidence