Hydrochloric Acid → 3-Hydroxy-4-iodobenzoic acid

Participants

Reaction Steps

3-Hydroxybenzoic acid (13.8 g, 100 mmol) is dissolved in concentrated NH4OH (200 mL) using an overhead stirrer and is treated slowly dropwise with a solution of iodine (23.4 g, 92 mmol) and KI (18.26 g, 110 mmol) in water (100 mL). The solution is stirred for 1 h at rt and then treated rapidly dropwise with concentrated HCl (180 mL). The white solid is collected via filtration, rinsed with water and dried overnight [by pulling air through the solid] in vacuo to afford 13.05 g (54%) of 3-hydroxy-4-iodobenzoic acid as a tan solid. 1H NMR (DMSO-d6): δ 7.13, 7.43, 7.80, 10.71, 12.98 ppm.

Provenance & Evidence