Water → HCID 11076628, compound

HRID 1792313Notes

Reaction equation

HRID 1792313 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][OH:8].[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1.O>N1C=CC=CC=1>[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15]([O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8134Diethylene Glycol Monomethyl Ether

Product 1

HCID 11076628HCID 11076628, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of diethylene glycol monomethylether (12 g, 100 mmol) in pyridine (70 ml) was added p-toluenesulfonyl chloride (22.8 g, 120 mmol) at 0° C., which was then stirred at room temperature for 2 hours. Water was added thereto, and the mixture was extracted with diethyl ether. The extracted organic layer was washed with 0.5N-HCl, water and saturated sodium bicarbonate solution, and dried over anhydrous magnesium sulfate. The organic solvent was removed under reduced pressure to give the title compound (27 g, stoichiometric yield) as a yellow oil. The compound thus obtained was used in the next reaction without further purification.

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe extracted organic layer was washed with 0.5N-HCl, water and saturated sodium bicarbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe organic solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8c8a90937fc941d6aa4e1f527bfdf07d
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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