反应 #1929017

反应方程式

ethylene glycol

p-Toluenesulfonyl chloride

HCl

→

bis(p-toluenesulfonyl)ethylene glycol

收率 83.0%

溶剂

pyridine

pyridine

反应条件

后处理

1. 1
   温度the 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
   其他The solid formed during this addition
7. 7
   过滤is filtered off
8. 8
   workup.DISSOLUTIONThis solid is dissolved
9. 9
   温度in refluxing methanol (250 ml)
10. 10
    其他the new precipitate formed
11. 11
    其他after returning to ambient temperature
12. 12
    过滤is filtered off
13. 13
    其他Finally, the white solid obtained
14. 14
    其他is dried under vacuum
15. 15
    其他the pure product is obtained (92.4 g, yield 83%)

实验过程

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%).

来源