Sodium Iodide → 3-tert-Butyl-4-hydroxy-5-iodobenzoic Acid

Participants

Reaction Conditions

Reaction Steps

20 g (103 mmol) of 3-tert-butyl-4-hydroxybenzoic acid are dissolved in 400 mL of methanol. 4.12 g (103 mmol) of sodium hydroxide and 15.4 g (103 mmol) of sodium iodide are added. The reaction medium is cooled to 0° C., and 234 g (113 mmol) of 3.6% sodium hypochlorite are added slowly. The medium is stirred at 0° C. for 2 hours and is then treated with saturated sodium thiosulfate solution. The aqueous phase is acidified and extracted with ethyl ether. A pale yellow solid is obtained (m=24.7 g; yield=75%; m.p.=178° C.).

Provenance & Evidence