Allyl bromide → HCID 23442858, compound

Participants

Reaction Steps

Under a nitrogen stream, 4.48 g of 3-t-butyl-4-trimethylacetoxyphenol synthesized in Example 15-2) was dissolved in 20 ml of dimethylformamide and a suspension of 0.86 g of oily sodium hydride in 20 ml of dimethylformamide at 0° C. was added dropwise. After stirring for 30 minutes, 1.86 ml of allyl bromide was added dropwise and the solution was stirred for 3 hours and allowed to attain room temperature. After the reaction was quenched with a saturated aqueous ammonium chloride solution, the mixture was extracted with water and n-hexane. 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 1% ethyl acetate) to give 4.31 g of 3-t-butyl-4-trimethylacetoxy-1-(2-propenyloxy)benzene as a colorless oil (yield 83%).

Provenance & Evidence