Sulfuric Acid → (3-Iodo-2-methylphenyl)methanol

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 3-hydroxymethyl-2-methylaniline hydrochloride from step A above and 17.2 ml of concentrated sulfuric acid in ice-water was cooled to 0° C., and a solution of 17.3 g (0.25 mole) of sodium nitrite in water was added dropwise. Upon complete addition the reaction mixture was stirred for an additional 0.5 hour, then an additional 8 ml of concentrated sulfuric acid was added dropwise. With the reaction mixture temperature still being maintained at 0° C., a solution of 49.8 g (0.30 mole) of potassium iodide in water was added dropwise, followed by the addition of 0.1 g of copper powder. The cooling bath was removed and the reaction mixture was slowly warmed to 70° C. After 1 hour at 70° C. the reaction mixture was allowed to cool to ambient temperature and stand for 18 hours. Water was added and the mixture was extracted with chloroform. The chloroform extract was washed with a saturated aqueous solution of sodium bisulfite, then with water. The chloroform layer was dried, filtered, and the filtrate concentrated under reduced pressure to give 15.2 g of (3-iodo-2-methylphenyl)-methanol as a dark solid. The nmr and ir spectra were consistent with the proposed structure.

Provenance & Evidence