Sesamol → Ethanone, 1-(6-hydroxy-1,3-benzodioxol-5-yl)-

Participants

Reaction Conditions

Reaction Steps

A solution of sesamol (5.6 g, 40 mmol) in acetic anhydride (20 mL) was cooled to 0° C. under an argon atmosphere. The solution was slowly added with boron trifluoride/diethyl ether complex (10 mL), and then the mixture was stirred at 90° C. for 2 hours. The reaction mixture was added to saturated aqueous sodium acetate (50 mL), and the mixture was stirred at room temperature. The solid formed was removed by filtration, and then the reaction mixture was extracted with ethyl acetate, and the organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residual solid was suspended in methanol, thereby washed, then collected by filtration and dried to obtain 1-(6-hydroxybenzo[d][1,3]dioxol-5-yl)ethanone (5.9 g, 82%).

Provenance & Evidence