Methanol → Methyl 4-hydroxy-3,5-diiodobenzoate

Participants

Reaction Steps

To a stirring solution of 3,5-diiodo-4-hydroxybenzoic acid (10.00 g, 25.65 mmol) in dry methanol (250 mL) was added TiCl4 (1.41 mL, 12.82 mmol) in one lot. The reaction was stirred at reflux for 6 h and was then stirred at room temperature for 24 h. The mixture was concentrated down and the residue was taken up in diethyl ether and filtered through a plug of silica gel. The filtrate was concentrated down and the residue was recrystallized from hot methanol to give 7.84 g (76%) of the ester as white crystalline needles. 1H NMR (DMSO-d6) δ 10.41 (br s, 1H), 8.22 (s, 2H), 3.79 (s, 3H).

Provenance & Evidence