4-Toluenesulfonyl chloride → 2-(Benzyloxy)ethyl 4-methylbenzenesulfonate

HRID 258423Notes

Reaction equation

HRID 258423 reaction equation
[H-].[Na+].[CH2:3]([O:10][CH2:11][CH2:12][OH:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>COCCOC>[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20]([O:13][CH2:12][CH2:11][O:10][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 121412-(Benzyloxy) ethanolHCID 24758Sodium hydride

Product 1

HCID 5613752-(Benzyloxy)ethyl 4-methylbenzenesulfonateYield 78.3%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a slurry of sodium hydride (0.4 g,17 mmol) in 20 ml ethylene glycol dimethyl ether cooled with an ice bath under an atmosphere of nitrogen, a solution of 2-benzyloxyethanol (2.1 ml, 15 mmol) and p-toluene sulfonyl chloride (2.9 g, 15 mmol) in ethylene glycol dimethyl ether was added dropwise. When the addition was complete, the ice bath was removed and the solution stirred at room temperature for 18 hours. After dilution with diethyl ether, the resulting slurry was filtered through anhydrous magnesium sulfate and concentrated under vacuum to yield 3.6 g of crude 2-benzyloxyethyl p-toluenesulfonate.

Workup

  1. additionWhen the addition
  2. customthe ice bath was removed
  3. filtrationAfter dilution with diethyl ether, the resulting slurry was filtered through anhydrous magnesium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f5e8f4949dc14dcea337fddbd0ef2f51
Source dataset
uspto-grants-1993_11
Patent number
US05266722

Reaction notes

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