tert-BUTYL CHLORIDE → 2-Tert-butylpyrene

Participants

Reaction Steps

A mixed solution of 100 g of pyrene, 55.4 g of t-butylchloride and 400 ml of dichloromethane was cooled to 0° C. under an argon gas stream and then 70.4 g of aluminum chloride was added. This mixed solution was stirred at room temperature for 5 hours and poured into 500 g of ice, followed by stirring at room temperature for 30 minutes. After the mixed solution was suction-filtered, the filtrate was extracted twice with 300 ml of dichloromethane. The organic layer was washed with 300 ml of water, dried over magnesium sulfate and then evaporated. To the concentrated residue, 300 ml of methanol was added, followed by stirring at 80° C. and further filtration. Furthermore, 300 ml of methanol was added, followed by stirring at 80° C. and further filtration. To 59.1 g of the crude product obtained by vacuum drying among 110.7 g of the crude product, 150 ml of methanol was added. The resulting solution was stirred at 85° C. for one hour, filtered and then vacuum-dried to obtain 50.3 g (content: 83%) of 2-t-butylpyrene.

Provenance & Evidence