Methanol → Methyl 2-methyl-5-nitrobenzoate

Participants

Reaction Conditions

Reaction Steps

To methanol (150 ml) at 0° C. under nitrogen was added dropwise thionyl chloride (4.0 ml, 54.8 mmol) over 2 min. The mixture was stirred at 0° C. for 15 min, before adding a solution of 2-methyl-5-nitrobenzoic acid (4.99 g, 27.5 mmol) in methanol (50 ml) by cannula over 5 min. The mixture was then allowed to warm to room temperature before heating at 50° C. for 18 h under nitrogen. The solvents were evaporated in vacuo and the residue stirred with water (100 ml) and dichloromethane (100 ml). The aqueous layer was basified with potassium carbonate, separated and reextracted with more dichloromethane (100 ml). The two organic extracts were combined, dried (MgSO4), and evaporated in vacuo to leave the title compound (5.24 g, 98%) as a white solid. 1H NMR (360 MHz, CDCl3) δ 2.72 (3H, s), 3.96 (3H, s), 7.44 (1H, d, J=8.3 Hz), 8.24 (1H, dd, J=8.4 and 2.6 Hz), 8.78 (1H, d, J=2.6 Hz).

Provenance & Evidence