Dimethyl Sulfoxide → HCID 22023911, compound

8 ml of Eaton's Reagent (from Aldrich, 7.7 wt. % of P2O5 in methanesulfonic acid) through an addition funnel to a mixture of 2.44 g (0.02 mol) of 2,6-dimethylphenol and 1.56 g (0.02 mol) of dimethylsulfoxide in a 50-mL 3-necked round bottom flask equipped with a thermometer, N2 inlet and magnetic stirrer. The rate of the addition was adjusted so that the temperature of the mixture did not rise above 60° C. during addition. After the exotherm had subsided, the reaction mixture was stirred at room temperature for 2 hours and then poured into 40 mL of distilled water. The solution was neutralized to pH=7 by adding ammonium hydroxide solution. The resulting solution was stirred at room temperature for half an hour and then filtered through a filter paper to remove the brown oily side products. The filtrate was added dropwise to a solution of 6.76 g (0.02 mol) of potassium perfluorobutanesulfonate (KPFBuS) in 70 mL water while stirring. The mixture was further stirred overnight. The white precipitate was collected by suction filtration and washed with water and ether three times. The crude product was redissolved in 15-20 mL of ethyl acetate. To this solution, 200-300 mg of aluminum oxide (activated, basic) was added. The mixture was rolled on a roller overnight and then filtered through Celite. The filtrate was precipitated into 100 mL ether while stirring. The white precipitate was collected and further washed with ether three times. Final yield: 2.2 g (23%).

1. additionThe rate of the addition
2. additiondid not rise above 60° C. during addition
3. stirringThe resulting solution was stirred at room temperature for half an hour
4. filtrationfiltered through a filter paper
5. customto remove the brown oily side products
6. stirringwhile stirring
7. waitThe mixture was further stirred overnight
8. filtrationThe white precipitate was collected by suction filtration
9. washwashed with water and ether three times
10. dissolutionThe crude product was redissolved in 15-20 mL of ethyl acetate
11. additionTo this solution, 200-300 mg of aluminum oxide (activated, basic) was added
12. customwas rolled on a roller overnight
13. filtrationfiltered through Celite
14. customThe filtrate was precipitated into 100 mL ether
15. stirringwhile stirring
16. customThe white precipitate was collected
17. washfurther washed with ether three times

ORD record

ord-e163e71d104641feb1debd0236ce8550

Source dataset

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07314700B2