Reaction #364867

Reaction equation

ethyl acetate

3,3,3,2,1,1-hexafluoropropane sulfonic acid

ditolyl sulfoxide

4-cyclohexylbenzene

phosphorus pentaoxide metanesulfonic acid

→

contemplated material

bis-(4-methylphenyl)4-cyclohexylphenyl sulfonium 3,3,3,2,1,1-hexafluoropropane sulfonate

Solvents

water

Conditions

Workup

1. 1
   Otherwas placed in a 125 ml flask
2. 2
   OtherThus, a dark brown solution was obtained
3. 3
   OtherAfter the exothermic reaction
4. 4
   workup.STIRRINGthe mixture was stirred at 45° C. for additional 3 hours
5. 5
   Otherwas then returned to room temperature
6. 6
   FiltrationThe slightly suspended solution was filtered
7. 7
   Otherto yield a white oil
8. 8
   workup.STIRRINGThe oil was stirred for 1 hour
9. 9
   ExtractionThe mixture was extracted
10. 10
    WashThe organic phase was washed several times with water
11. 11
    Otherdried
12. 12
    OtherThe solvent was removed by distillation
13. 13
    OtherThe oily residue was recrystallized from ethyl acetate and diethyl ether

Procedure

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).

Source