Methanol → Methyl 5-nitrosalicylate

Participants

Reaction Steps

Thionyl chloride (30 ml) was added dropwise to a solution of 5-nitro salicyclic acid (25 g) in methanol (300 ml) over 30 minutes. After stirring at room temperature for 18 hours the solvent and excess thionyl chloride was removed on a rotary evaporator. The residue was dissolved in hot toluene, filtered and cooled. A white solid methyl-2-hydroxy-5-nitro-benzoate was isolated by filtration. This material was treated with acetic anhydride (20 ml) and sulfuric acid (8 drops) at 50° C. for 1 hour. The reaction was cooled, poured into cold water (250 ml), stirred for 30 minutes and the title compound was isolated by vacuum filtration. This material was washed well with water, m.p. ca. 70°-72° C.

Provenance & Evidence