Chloroform → 3-Nitro-alpha-(trichloromethyl)benzenemethanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-nitrobenzaldehyde (80 g, 0.53 mol) and chloroform (95 ml, 1.17 mol) in 320 ml of N-methylpyrrolidinone cooled to -10° C. under nitrogen was added dropwise a solution of potassium hydroxide (24 g, 0.43 mol) in 80 ml of methanol over a 40 minute period. The deep purple reaction mixture was aged for 4 hours at -5° C. before quenching into 640 ml of lN HCl and 500 ml of methylene chloride cooled to 0° C. The quench mixture was stirred and cooled for an additional 0.5 hour and then brought to ambient temperature. The methylene chloride layer was separated and washed twice with 720 ml of water, 720 ml of 10% sodium bisulfite, and again with 720 ml of water. After treatment with 9.0 g of Darco G-60 charcoal for 1 hour and filtration through Super-Cel, the organic layer was washed with 450 ml of aqueous 5% sodium bicarbonate solution and then 720 ml of water, with 65 ml of saturated salt solution added. The resulting methylene chloride solution contained 140.2 g (98.4% yield) of TMBA.

Provenance & Evidence