Bromocycloheptane → HCID 23442891, compound

Participants

Reaction Steps

To 2.36 g of 5-acetoxy-4-t-butyl-2-hydroxybenzaldehyde dissolved in 10 ml of anhydrous tetrahydrofuran was added 0.40 g of oily sodium hydride under nitrogen atmosphere and the mixture was stirred at room temperature for 30 minutes. Then, 23 ml of a Grignard reagent (0.43 M in tetrahydrofuran) which has been prepared from magnesium and cycloheptyl bromide was added dropwise to this reaction mixture and the mixture was stirred at room temperature for 1 hour. Then, the mixture was combined with a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layers were washed with saturated brine, then dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (in n-hexane containing 15% ethyl acetate) to give 0.77 g of 4-acetoxy-5-t-butyl-2-(cycloheptylhydroxymethyl)phenol as a colorless oil (yield 23%) and 0.72 g of 5-t-butyl-2-(cycloheptylhydroxymethyl)benzene-1,4-diol as a colorless oil (yield 25%).

Provenance & Evidence