3-Chloro-2-methyl-1-propene → HCID 23442874, compound

Participants

Reaction Steps

Under a nitrogen stream, a solution of 0.50 g of 2,5-di-t-butyl-4-trimethylacetoxyphenol in 3 ml of dimethylformamide was added dropwise into a suspension of 0.08 g of oily sodium hydride in 3 ml of dimethylformamide. After stirring for 30 minutes, 0.19 ml of methallyl chloride was added dropwise and the mixture 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 0.48 g of 2,5-di-t-butyl-4-trimethylacetoxy-1-(2-methyl-2-propenyloxy)benzene as a colorless oil (yield 82%).

Provenance & Evidence