Methanol → 4-Nitrosalicylic acid

Participants

Reaction Steps

To a solution of 2-methoxy-4-nitro-benzoic acid (20 g, 0.102 mol) in 80 ml of CH2Cl2 at 0° C. was added BBr3 (1.0 M, 150 ml, 1.5 eq.). The resulting mixture was allowed to warm to rt and stirred for 2 h. MeOH was then added dropwise to quench the reaction at 0° C. and the volatile fraction was removed in vacuo. The residue was purified on a silica gel column with 6/4/0.3 of hexane, EtOAc and HOAc to give 18 g of 2-hydroxy-4-nitro-benzoic acid (M+: 183).

Provenance & Evidence