Methanol → Methyl 3-hydroxy-4-nitrobenzoate

Participants

Reaction Conditions

Reaction Steps

3-Hydroxy-4-nitro-benzoic acid 1a (3.17 g, 17.32 mmol) was dissolved in 40 mL of anhydrous methanol. The reaction solution was cooled down to 0° C. and added dropwise with thionyl chloride (3.09 g, 25.98 mmol) with stirring. Upon the completion of the addition, the resulting solution was heated to reflux for 2 hours. The reaction solution was concentrated under reduced pressure, extracted with ethyl acetate (200 mL). The combined organic phase was washed with saturated sodium bicarbonate solution (100 mL×3), saturated sodium chloride solution (100 mL×3) successively, then dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure to obtain the title compound methyl 3-hydroxy-4-nitro-benzoate 1b (3.30 g as a yellow solid) yield: 96.7%.

Provenance & Evidence