Sodium Iodide → 4-Iodo-2-propylphenol

Participants

Reaction Steps

A mixture of 6.8 g (50 mmol) of 2-propylphenol, 8.25 g (55 mmol) of sodium iodide, 175 ml of acetonitrile and 40 ml of water was cooled on ice. t-Butylhypochlorite, 6 g or 6.56 ml (55 mmol), was added slowly at 0°. After stirring for 10 minutes at 0°, 500 ml of ethyl acetate was added and the mixture was washed with 5% aqueous solution of sodium thiosulfate. The organic layer was dried and evaporated and the residue was chromatographed over 150 g of silica gel using methylene chloride/hexane 3:2. The more polar monoiodinated product was crystallized from petroleum ether to give colorless crystals with m.p. 54°-56°.

Provenance & Evidence