Toluene → HCID 67954229, compound

Participants

Reaction Steps

A glass flask fitted with a thermometer and a condenser was charged with 100 g (0.52 mol) of trifluoromethanesulfonamide ethanol, 108.6 g (0.54 mol) of 1-adamantanecarboxylic acid, para-toluenesulfonic acid (0.1 mol) and 500 g of toluene, and a Dean-Stark dehydration apparatus was used to perform dehydration under reflux conditions. Refluxing for 9 hours enabled removal of approximately 9 ml of water. The resulting reaction mixture was dissolved in 500 g of ethyl acetate, and the thus obtained solution was washed twice with a saturated solution of sodium bicarbonate, once with 1N—HCl, and once with a saturated solution of sodium chloride. The organic phase was then dried over sodium sulfate, the solvent was removed by distillation under reduced pressure, and the product was recrystallized in hexane, yielding 140 g of N-[2-(adamantan-1-ylcarbonyloxy)ethyl]trifluoromethanesulfonamide (yield: 75%, purity: 99%).

Provenance & Evidence