Reaction #1929017

Reaction equation

ethylene glycol

p-Toluenesulfonyl chloride

HCl

→

bis(p-toluenesulfonyl)ethylene glycol

Yield 83.0%

Solvents

pyridine

pyridine

Conditions

Workup

1. 1
   Temperaturethe 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
   OtherThe solid formed during this addition
7. 7
   Filtrationis filtered off
8. 8
   workup.DISSOLUTIONThis solid is dissolved
9. 9
   Temperaturein refluxing methanol (250 ml)
10. 10
    Otherthe new precipitate formed
11. 11
    Otherafter returning to ambient temperature
12. 12
    Filtrationis filtered off
13. 13
    OtherFinally, the white solid obtained
14. 14
    Otheris dried under vacuum
15. 15
    Otherthe pure product is obtained (92.4 g, yield 83%)

Procedure

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%).

Source