Hydrochloric Acid → Tetraethylene glycol ditosylate

HRID 2249293Notes

Reaction equation

HRID 2249293 reaction equation
[CH2:1]([OH:13])[CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][OH:12].[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.[OH2:25].Cl>N1C=CC=CC=1>[S:20]([O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][O:3][CH2:2][CH2:1][O:13][S:20]([C:17]1[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=1)(=[O:21])=[O:25])([C:17]1[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=1)(=[O:22])=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8200Tetraethylene Glycol

Product 1

HCID 3706987Tetraethylene glycol ditosylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1.64 g (8.44 mmol) of tetraethylene glycol in dry pyridine (30 ml) was added 3.55 g (18.6 mmol) of p-toluenesulfonyl chloride in an atmosphere of argon, and the mixture was allowed to react at room temperature for 15 hours. To the solution was added water followed by addition of conc. hydrochloric acid to adjust the pH to 4, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography for separation and purification. Elution with dichloromethane-methanol (100:1) yielded 3.78 g (7.52 mmol) of O,O'-ditosyl-3,6,9-trioxaundecane-1,11-diol.

Workup

  1. customto react at room temperature for 15 hours
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. concentrationconcentrated under reduced pressure
  5. customThe residue thus obtained
  6. customwas subjected to silica gel column chromatography for separation and purification
  7. washElution with dichloromethane-methanol (100:1)

Sources & evidence

ORD record
ord-df6772b71f814c90a69a677fac502790
Source dataset
uspto-grants-1991_08
Patent number
US05043142

Reaction notes

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