(Aminomethyl)phosphonic acid → 4,5-epoxy-N-allylcyclohexane-1,2-dicarboximide

Participants

Reaction Steps

In a 50 ml three-necked flask equipped with a reflux condenser, thermometer, stirrer, dropping funnel and oil bath there were charged 100.0 g of N-allyl-4-cyclohexene-1,2-dicarboximide, 2.44 g of methyltrioctylammonium hydrogensulfate, 3.45 g of sodium tungstate dihydrate and 0.58 g of aminomethylphosphonic acid. The mixture was heated using an oil bath kept at 90° C., and after adding 80 ml of 30% hydrogen peroxide water dropwise over a period of 180 minutes through a dropping funnel, the mixture was aged for 4 hours. After cooling with an ice bath and removing the excess hydrogen peroxide with 300 ml of saturated aqueous sodium thiosulfate, extraction was performed twice with 200 ml of ethyl acetate. The obtained ethyl acetate solution was dried overnight over anhydrous sodium sulfate, and a rotary evaporator was used to remove the ethyl acetate solvent, after which purification was performed with a chromatography column packed with 25% hydrous silica gel to obtain 78.9 g of 4,5-epoxy-N-allylcyclohexane-1,2-dicarboximide.

Provenance & Evidence