Diethyl Ether → alpha-Hydroxy-2-nitro-3-phenylbenzofuran-7-acetonitrile

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 2.7 g. (0.010 mole) of 2-nitro-3-phenylbenzofuran-7-aldehyde and 20 ml. of diethyl ether is treated with 1.6 g. (0.015 mole) of sodium bisulfite in 10 ml. of water. After 30 minutes, 30 ml. of chloroform is added and then, 30 minutes later, 1.5 g. (0.030 mole) of sodium cyanide in 5 ml. of water is added. One-half hour after that 0.7 g. of sodium bisulfite is added, then, after another 30 minutes, the mixture is cooled at 0° C. for about 16 hours. The organic layer is separated, washed with aqueous sodium bisulfite solution, then with water, and dried over magnesium sulfate. Evaporation of the solution provides a solid which is recrystallized from a chloroform-heptane mixture to provide yellow crystals of α-hydroxy-2-nitro-3-phenylbenzofuran-7-acetonitrile, m.p. 137°-139° C.

Provenance & Evidence