Hydrochloric Acid → 3-Hydroxy-3,3-diphenylpropanenitrile

Participants

Reaction Conditions

Reaction Steps

The starting material is prepared as follows: The solution of 650 ml of molar n-butyl lithium in hexane is diluted with 650 ml of dry tetrahydrofuran and the mixture stirred and cooled to -70° C. under a nitrogen atmosphere. Then the solution of 37.2g of acetonitrile in 800 ml of tetrahydrofuran is added steadily over a period of 15 minutes. The resulting suspension is stirred at -70° C. for 1 hour before the solution of 165 g of benzophenone in 800 ml of tetrahydrofuran is added steadily over 15 minutes. When addition is complete, the mixture is stirred without external cooling for 20 minutes, and then poured onto a mixture of 1.5 kg of crushed ice and 200 ml of 6N hydrochloric acid. The organic layer is separated and the aqueous solution extracted with diethyl ether. The combined organic solutions are dried and evaporated to give the β-hydroxy-β,β-diphenyl-propionitrile melting at 135°-8°.

Provenance & Evidence