Sodium Hydroxide → 3-Methyl-5-nitrobenzoic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 89A (0.36 g, 1.8 mmol) and aqueous sodium hydroxide (1N, 3 mL, 3 mmol) in a mixture of methanol (1.5 mL) and tetrahydrofuran (3 mL) was heated at 80° C. for 1 h and at rt for 2 h. An additional portion of sodium hydroxide solution (1 mL) was added and the mixture was heated at 80° C. for 5 min. The reaction mixture was concentrated in vacuo, diluted with ethyl acetate and acidified with hydrochloric acid (1N). The aqueous layer was extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried (MgSO4), and concentrated in vacuo to give 89B (0.314 g, 94%) as a white solid. LCMS: 182 (M+1)

Provenance & Evidence