Methanol → Methyl 3-hydroxy-4-iodobenzoate

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask containing 3-hydroxy-4-iodobenzoic acid (1.0346 g, 3.92 mmol, commercially available from Aldrich) was added a cold solution of MeOH (15 mL) and sulfuric acid (0.5 mL). The mixture was heated to 80° C. and monitored with TLC. After 20.5 hours, the solvent was removed and the residue was diluted with EtOAc. The organic phase was washed carefully two times with saturated aqueous NaHCO3, once with brine, and then dried over anhydrous sodium sulfate. After filtration, the organic solvent was removed in vacuo to afford 83.26A as a white solid (1.0938 g, 100% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.76 (1H, d, J=8.2 Hz), 7.64 (1H, d, J=2.0 Hz), 7.34 (1H, dd, J=8.2, 2.0 Hz), 3.92 (3H, s).

Provenance & Evidence