Methanol → Methyl 3-iodo-4-methylbenzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-iodo-4-methyl-benzoic acid (10.0 g, 38.2 mmol) in methanol (70 ml) is added concentrated sulfuric acid (0.5 ml). The reaction mixture is heated at 70° C. for 48 hours, cooled to room ambient temperature and then concentrated. After that, ethyl acetate (100 ml) and aqueous NaHCO3 (saturated, 100 ml) solution are added to the residue. The organic layer is separated and washed again with aqueous NaHCO3 (saturated, 100 ml) solution. The organic layer is separated, dried over anhydrous Na2SO4 and concentrated to yield 3-iodo-4-methyl-benzoic acid methyl ester 1. It is used without further purification in the next step. 1H NMR (400 MHz, DMSO-d6) δ 8.31 (s, 1 H), 7.87 (d, 1 H, J=8.4 Hz), 7.48 (d, 1 H, J=8.4 Hz), 3.85 (s, 3 H), 3.35 (s, 3 H); LC-MS m/z: 277.0 (M+1).

Provenance & Evidence