Hydrochloric Acid → 5-Chloro-2-nitrobenzyl alcohol

Participants

Reaction Conditions

Reaction Steps

A solution of borane:tetrahydrofuran complex (25.8 g, 0.3 mole) in tetrahydrofuran (THF) (300 mL) was added dropwise to a stirred solution of 5-chloro-2-nitrobenzoic acid (50.0 g, 0.24 mole) in dry THF (400 mL) maintained at 0° C. under an atmosphere of nitrogen. After completion of the addition, the mixture was heated at 50° C. for 96 hours before being cooled in an ice bath. Hydrochloric acid (10% solution) was added dropwise and the mixture refluxed for 30 minutes. The THF was removed in vacuo and the residue extracted with dichloromethane (3×350 mL). Combined extracts were washed with saturated sodium bicarbonate solution, dried over magnesium sulfate and the solvent evaporated to give a solid (45 g, 100%), crystallization from chloroform-hexane gave 5-chloro-2-nitro-benzenemethanol (41.0 g, 91%) mp 79°-81° C.

Provenance & Evidence