Sodium Iodide → HCID 54112049, compound

Participants

Reaction Steps

5.00 g of 3-t-butyl-4-trimethylacetoxyanisole was dissolved in 45 ml of acetonitrile and 4.54 g of sodium iodide was added at room temperature under a nitrogen stream and 3.84 ml of trimethylsilyl chloride was further added dropwise. This solution was refluxed for 6 hours, then poured into a saturated aqueous sodium bicarbonate solution and extracted with diethyl ether. The organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (in n-hexane containing 17% ethyl acetate) to give 4.50 g of 3-t-butyl-4-trimethylacetoxyphenol as a white solid (yield 95%).

Provenance & Evidence