반응 #1929017

반응 방정식

ethylene glycol

p-Toluenesulfonyl chloride

HCl

→

bis(p-toluenesulfonyl)ethylene glycol

수율 83.0%

용매

pyridine

pyridine

반응 조건

후처리

1. 1
   온도the solution is cooled with an ice bath
2. 2
   workup.ADDITIONThe temperature must remain below 20° C. during the addition
3. 3
   workup.ADDITIONWhen approximately 90 g have been added
4. 4
   workup.WAITThe reaction mixture is left
5. 5
   workup.STIRRINGstirring for 2 h 30
6. 6
   기타The solid formed during this addition
7. 7
   여과is filtered off
8. 8
   workup.DISSOLUTIONThis solid is dissolved
9. 9
   온도in refluxing methanol (250 ml)
10. 10
    기타the new precipitate formed
11. 11
    기타after returning to ambient temperature
12. 12
    여과is filtered off
13. 13
    기타Finally, the white solid obtained
14. 14
    기타is dried under vacuum
15. 15
    기타the pure product is obtained (92.4 g, yield 83%)

실험 절차

19.8 g (0.3 mol) of ethylene glycol are dissolved in 150 ml of distilled pyridine and then the solution is cooled with an ice bath. p-Toluenesulfonyl chloride (123 g, 0.65 mol) is added slowly with mechanical stirring. The temperature must remain below 20° C. during the addition. When approximately 90 g have been added, stirring becomes difficult and the mixture is diluted with 200 ml of pyridine. The reaction mixture is left stirring for 2 h 30. An aqueous HCl solution (12N HCl (170 ml) in ice (500 ml)) is added. The solid formed during this addition is filtered off. This solid is dissolved in refluxing methanol (250 ml) and then the new precipitate formed after returning to ambient temperature is filtered off. Finally, the white solid obtained is dried under vacuum and the pure product is obtained (92.4 g, yield 83%).

출처