反応 #1929017

反応方程式

ethylene glycol

p-Toluenesulfonyl chloride

HCl

→

bis(p-toluenesulfonyl)ethylene glycol

収率 83.0%

溶媒

pyridine

pyridine

反応条件

後処理

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

実験手順

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%).

出典