تفاعل #2336535

معادلة التفاعل

N2

Eaton's Reagent

2,6-dimethylphenol

dimethylsulfoxide

potassium perfluorobutanesulfonate

ammonium hydroxide

→

dimethyl (3,5-dimethyl)-4-hydroxyphenyl sulfonium perfluorobutane sulfonate

المذيبات

water

water

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONThe rate of the addition
2. 2
   workup.ADDITIONdid not rise above 60° C. during addition
3. 3
   workup.STIRRINGThe resulting solution was stirred at room temperature for half an hour
4. 4
   ترشيحfiltered through a filter paper
5. 5
   أخرىto remove the brown oily side products
6. 6
   workup.STIRRINGwhile stirring
7. 7
   workup.WAITThe mixture was further stirred overnight
8. 8
   ترشيحThe white precipitate was collected by suction filtration
9. 9
   غسيلwashed with water and ether three times
10. 10
    workup.DISSOLUTIONThe crude product was redissolved in 15-20 mL of ethyl acetate
11. 11
    workup.ADDITIONTo this solution, 200-300 mg of aluminum oxide (activated, basic) was added
12. 12
    أخرىwas rolled on a roller overnight
13. 13
    ترشيحfiltered through Celite
14. 14
    أخرىThe filtrate was precipitated into 100 mL ether
15. 15
    workup.STIRRINGwhile stirring
16. 16
    أخرىThe white precipitate was collected
17. 17
    غسيلfurther washed with ether three times

الإجراء التجريبي

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%).

المصدر