Methanol → Methyl 2-methyl-4-nitrobenzoate

Participants

Reaction Conditions

Reaction Steps

H2SO4 (98%, 0.030 mL) was added dropwise into the MeOH (30 mL) solution of 2-methyl-4-nitrobenzoic acid at rt. The mixture was then heated at 55° C. After 50 h, the solvent was removed in vacuo and the residue was partitioned between EtOAc and H2O (25 mL each). The aqueous layer was extracted with another portion of EtOAc (25 mL). The combined extracts were washed with saturated NaHCO3 (25 mL), H2O (2×25 mL), and brine (25 mL), dried over MgSO4, filtered and concentrated in vacuo to give the title compound as light-yellow solid. 1H NMR (CDCl3, 400 MHz): δ=2.69 (s, 3H), 3.95 (s, 3H), 8.03-8.12 (m, 3H). MS (ES+): m/z 196.25 (100) [MH+]. HPLC: tR=3.29 min (ZQ2000, polar—5 min).

Provenance & Evidence