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

HRID 703048Notes

Reaction equation

HRID 703048 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

An example is disclosed in U.S. patent application Ser. No. 269,205. 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-3d2385f3820147558e8bff3be2197ac7
Source dataset
uspto-grants-1991_01
Patent number
US04981648

Reaction notes

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