Ethylene Glycol → HCID 85876525, compound

HRID 1841835Notes

Reaction equation

HRID 1841835 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[C:5]1([CH3:15])[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1.Cl>N1C=CC=CC=1>[C:5]1([CH3:15])[CH:10]=[CH:9][C:8]([S:11]([CH:1]([OH:4])[CH:2]([OH:3])[S:11]([C:8]2[CH:9]=[CH:10][C:5]([CH3:15])=[CH:6][CH:7]=2)(=[O:13])=[O:12])(=[O:13])=[O:12])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 85876525HCID 85876525, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

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%).

Workup

  1. temperaturethe solution is cooled with an ice bath
  2. additionThe temperature must remain below 20° C. during the addition
  3. additionWhen approximately 90 g have been added
  4. waitThe reaction mixture is left
  5. stirringstirring for 2 h 30
  6. customThe solid formed during this addition
  7. filtrationis filtered off
  8. dissolutionThis solid is dissolved
  9. temperaturein refluxing methanol (250 ml)
  10. customthe new precipitate formed
  11. customafter returning to ambient temperature
  12. filtrationis filtered off
  13. customFinally, the white solid obtained
  14. customis dried under vacuum
  15. customthe pure product is obtained (92.4 g, yield 83%)

Sources & evidence

ORD record
ord-918f07fbd9734412a1de1a1bc3524da9
Source dataset
uspto-grants-2015_02
Patent number
US08945514B2

Reaction notes

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