Hydrogen Peroxide → 4,5-epoxy-N-allylcyclohexane-1,2-dicarboximide

Participants

Reaction Steps

100.0 g of N-allyl-4-cyclohexene-1,2-dicarboximide, 2.44 g of methyltrioctylammonium hydrogen sulfate, 3.45 g of sodium tungstenate dihydrate and 0.58 g of aminomethylphosphonic acid were charged into a 500 mL three-mouth flask provided with a reflux condenser, thermometer, stirring apparatus, dropping funnel and oil bath. After heating using the oil bath maintained at a temperature of 90° C., 80 ml of 30% aqueous hydrogen peroxide were dropped in over the course of 180 minutes through the dropping funnel followed by aging for 4 hours. After cooling with an ice bath and removing the excess hydrogen peroxide with 300 ml of saturated aqueous sodium thiosulfate solution, the reaction mixture was extracted twice with 200 ml of ethyl acetate. The resulting ethyl acetate solution was dried overnight with anhydrous sodium sulfate followed by removing the solvent ethyl acetate using a rotary evaporator and purifying by column chromatography using a column packed with 25% aqueous silica gel to obtain 78.9 g of 4,5-epoxy-N-allylcyclohexane-1,2-dicarboximide.

Provenance & Evidence