Sulfuric Acid → 4-t-Amylphenyliodonium sulfate

Participants

Reaction Steps

Sixty grams of t-amylbenzene, 39.5 g of potassium iodate, 81 g of acetic anhydride and 170 ml of dichloromethane were mixed, and 66.8 g of concentrated sulfuric acid was slowly added thereto under ice cooling. After stirring under ice cooling for 2 hours, the mixture was stirred at room temperature for 10 hours. To the reaction solution, 500 ml of water was added under ice cooling, and the resulting solution was extracted with dichloromethane. An organic phase was washed with sodium hydrogencarbonate and water, followed by concentration to obtain (4-t-amylphenyl)iodonium sulfate. This sulfate was added to an excess amount of the solution of tetramethylammonium pentafluorobnzenesulfonate. To this solution, 500 ml of water was added, and the resulting solution was extracted with dichloromethane. An organic phase was washed with a 5% aqueous solution of tetramethylammonium hydroxide and water, followed by concentration to obtain di(4-t-amylphenyl)iodonium pentafluorobenzenesulfonate.

Provenance & Evidence