Ethyl Acetate → Bis-(4-methylphenyl)4-cyclohexylphenyl sulfonium 3,3,3,2,1,1-hexafluoropropane sulfonate

Participants

Reaction Conditions

Reaction Steps

A mixture of 10.36 g (4.5 mmol) of ditolyl sulfoxide with 7.21 g (4.5 mmol) of 4-cyclohexylbenzene was placed in a 125 ml flask. Then 20 ml of a previously prepared phosphorus pentaoxide/metanesulfonic acid reagent (prepared by dissolving 36 g of phosphorus pentaoxide in 360 g of methanesulfonic acid) was added thereto while stirring with a magnetic stirrer. The mixture was heated to about 50° C. Thus, a dark brown solution was obtained. After the exothermic reaction ceased, the mixture was stirred at 45° C. for additional 3 hours. The temperature was then returned to room temperature, and the mixture was poured into 100 ml of water and 100 g of ice. The slightly suspended solution was filtered, followed by addition of 10.44 g (4.5 mmol) of 3,3,3,2,1,1-hexafluoropropane sulfonic acid to yield a white oil. The oil was stirred for 1 hour, and 200 ml of ethyl acetate was added thereto. The mixture was extracted. The organic phase was washed several times with water, and then dried. The solvent was removed by distillation. The oily residue was recrystallized from ethyl acetate and diethyl ether to give 11.5 g of the contemplated material. The structure was confirmed by 1H-NMR (CDCl3) with δ=1.08-1.74 (m, 10H), 2.41-2.43 (m, 7H), 5.27-5.48 (d[m], 1H), 7.16-7.19 (d, 2H), 7.43-7.46 (d, 4H), 7.50-7.53 (d, 4H), and 7.78-7.80 ppm (d, 2H).

Provenance & Evidence