4-Toluenesulfonyl chloride → 2-(2-Ethoxyethoxy)ethyl 4-methylbenzene-1-sulfonate

HRID 1167667Notes

Reaction equation

HRID 1167667 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][OH:9])[CH3:2].C(N(CC)CC)C.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>ClCCl>[CH3:27][C:17]1[CH:22]=[CH:21][C:20]([S:23]([O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][O:3][CH2:1][CH3:2])(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8146Diethylene Glycol Monoethyl EtherHCID 8471Triethylamine

Product 1

HCID 41182322-(2-Ethoxyethoxy)ethyl 4-methylbenzene-1-sulfonateYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

432 mg (3.22 mmol) of 2-(2-ethoxyethoxy)ethanol was dissolved in 40 ml of dichloromethane, and 0.6 ml (4.19 mmol) of triethylamine and 614 mg (3.22 mmol) of p-toluenesulfonyl chloride were added thereto. The mixture was stirred at room temperature for 15 hours. After the solvent was removed under reduced pressure, 40 ml of water was added thereto. The mixture was extracted with 30 ml of ethyl acetate. The solvent was removed under reduced pressure to give 760 mg (2.64 mmol) of the title compound in a yield of 82%.

Workup

  1. customAfter the solvent was removed under reduced pressure, 40 ml of water
  2. additionwas added
  3. extractionThe mixture was extracted with 30 ml of ethyl acetate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-394e249e55cc4633b205701916b87025
Source dataset
uspto-grants-2003_09
Patent number
US06620831B2

Reaction notes

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