Diisopropylamine → beta-Hydroxy-beta-(2-methoxyphenyl)-2-methoxybenzenepropanenitrile

Participants

Reaction Steps

As in Example 97, a solution of 2,2'-dimethoxybenzophenone (24.2 g) and acetonitrile (6 mL) in tetrahydrofuran (120 mL) was added to a chilled (-70° C.) solution of lithium diisopropylamide prepared from diisopropylamine (16 mL) and 1.55M n-butyl lithium in hexane (74 mL) in dry tetrahydrofuran (120 mL). After the reaction was kept at -70° C. for 15 minutes, it was allowed to warm to room temperature and then was worked up in the usual manner to furnish 26.4 g of beta-hydroxy-beta-(2-methoxyphenyl)-2-methoxybenzenepropanenitrile, mp 170°-180° C. A sample was recrystallized from methanol to give the analytical specimen, mp 181°-182° C.

Provenance & Evidence