Butylated Hydroxyanisole → 3-t-Butyl-4-trimethylacetoxyanisole

Participants

Reaction Steps

5.00 g of 3-t-butyl-4-hydroxyanisole was dissolved in 30 ml of dimethylformamide and the solution was added dropwise into a suspension of 1.33 g of oily sodium hydride in 30 ml of dimethylformamide at 0° C. under a nitrogen stream. After stirring for 30 minutes, 3.76 ml of trimethylacetyl chloride was added dropwise and the solution was stirred overnight and allowed to attain room temperature. After the reaction was quenched with a saturated aqueous ammonium chloride solution, the reaction solution was extracted with water and ethyl acetate. 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 3%-5% ethyl acetate) to give 5.25 g of 3-t-butyl-4-trimethylacetoxyanisole as a white solid (yield 72%).

Provenance & Evidence