Methanol → Methyl 2-(3-nitrophenyl)acetate

Participants

Reaction Conditions

Reaction Steps

Combine (3-nitrophenyl)acetic acid (20.0 g, 110 mmol) and anhydrous methanol (125 mL). Add 7 drops of concentrated sulfuric acid. Heat to 50° C. After 14 hours, cool to ambient temperature. Evaporate in vacuo to give a residue. Partition the residue between water and diethyl ether. Separate the organic layer and extract with aqueous saturated sodium bicarbonate solution and aqueous saturated sodium chloride solution. Dry the organic layer over MgSO4 and filter. Slowly evaporate to give methyl (3-nitrophenyl)acetate. 1H NMR (CDCl3) δ8.17 (d, 1H, J=1.1 Hz), 8.14 (dd, 1H, J=1.0, 7.7 Hz), 7.63 (dd, 1H, J=1.1, 7.7 Hz), 7.52 (t, 1H, J=7.7 Hz), 3.75 (s, 2H), 3.73 (s, 3H).

Provenance & Evidence