Hydrochloric Acid → 5-Hydroxy-2-nitrobenzoic acid

Participants

Reaction Steps

5-Chloro-2-nitrobenzoic acid (100 g) in 800 ml dimethylsulfoxide was treated with 112 g powdered KOH with cooling, 170 ml anhydrous alcohol added and the mixture stirred 2 hours at 25° and then left overnight. The mixture was kept at 28° for about 8 hours, then overnight at 0°, warmed to room temperature and 3.5 liters of water added. The mixture was acidified with HCl, 1 kg NcCl added and extracted with ethyl acetate. The extract was washed with water, dried, 50 g KHCO3 in 500 ml water added, diluted to 2 liters, and the ethyl acetate blown off with a stream of nitrogen. The solution was acidified and filtered to give 56 g product, m.128-30°.

Provenance & Evidence