Methanol → Methyl 3-iodo-4-methylbenzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-iodo-4-methylbenzoic acid (28.0 g, 0.107 mol) in MeOH (300 mL) at 0° C. was carefully added concentrated H2SO4 (30 mL). The mixture was heated at 60° C. overnight, then cooled and the solvent removed under reduced pressure. The residue was carefully poured onto ice-water (200 mL) and the mixture was extracted with EtOAc (500 mL). The organics was washed with water (100 mL), saturated NaHCO3 (100 mL), brine (100 mL), dried (MgSO4), filtered, and concentrated to yield the title compound as a brown oil (29.0 g, 98%). 1H NMR (400 MHz, CDCl3) δ 8.47 (d, J=1.7 Hz, 1H), 7.90 (dd, J=7.9 Hz, 1.7 Hz, 1H), 7.29 (d, J=7.9 Hz, 1H), 3.90 (s, 2H), 2.48 (s, 3H).

Provenance & Evidence