Hydrochloric Acid → 5-(Methylsulfanyl)-2-nitrobenzoic acid

Participants

Reaction Conditions

Reaction Steps

5-Chloro-2-nitrobenzoic acid (25.2 g, 0.125 mol) was stirred in water. To this was added sufficient sodium hydroxide solution (2M, 42 ml, 0.084 mol) to dissolve the acid completely. A solution of sodium sulfide nonahydrate (33.0 g, 0.1375 mol) in water (75 ml) was added and the solution was stirred at 60° C. for 2.5 hr. This resultant red solution was added to a solution of sodium hydroxide (50% 10 ml, 0.125 mol) in water (15 ml), dimethyl sulfate (24 ml, 0.25 mol) was added and the solution heated under reflux for 1 hour. The solution was cooled and acidified with hydrochloric acid (5M, 32 ml, 0.16 mol). The precipitated yellow solid was filtered off, washed with water, dried at 60° C. under vacuum, mp 173° C. (lit. J. Heterocyclic Chemistry 1981 18 117). Mp 175-178° C.)

Provenance & Evidence