Ethylene Glycol → HCID 85876525, compound

HRID 980784Notes

Reaction equation

HRID 980784 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[S:5](Cl)([C:8]1[CH:14]=[CH:13][C:11]([CH3:12])=[CH:10][CH:9]=1)(=[O:7])=[O:6]>N1C=CC=CC=1>[C:11]1([CH3:12])[CH:13]=[CH:14][C:8]([S:5]([CH:1]([OH:4])[CH:2]([OH:3])[S:5]([C:8]2[CH:14]=[CH:13][C:11]([CH3:12])=[CH:10][CH:9]=2)(=[O:7])=[O:6])(=[O:7])=[O:6])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 85876525HCID 85876525, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

Twenty-eight ml of ethylene glycol and 100 ml of pyridine were added over a 2.5 hour period to a stirred mixture of tosyl chloride (210 g) in pyridine (225 ml), with the mixture being cooled by a water bath. After stirring for several hours, the mixture was shaken with one liter of ice water for about ten minutes and then filtered. The residue was washed with ether, dilute sulfuric acid, water, and finally ether. (Each of the washed liquids was ice cold.) The residue was then dried by vacuum pumping and recrystallized from boiling acetonitrile. The recrystallized residue, yield 75%, had a melting point of 123° to 125° C.

Workup

  1. temperaturebeing cooled by a water bath
  2. filtrationfiltered
  3. washThe residue was washed with ether, dilute sulfuric acid, water, and finally ether
  4. custom) The residue was then dried by vacuum
  5. customrecrystallized

Sources & evidence

ORD record
ord-fee5e1dc3ec941799f9adf1cb7496de0
Source dataset
uspto-grants-1987_01
Patent number
US04639365

Reaction notes

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