1,2-Dimethoxyethane → 2-(Benzyloxy)ethyl 4-methylbenzenesulfonate

HRID 258422Notes

Reaction equation

HRID 258422 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:12]1(C)[C:13]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:15]=[CH:16][CH:17]=1.[H-].[Na+].[CH3:25]OCCOC>>[C:16]1([CH3:25])[CH:17]=[CH:12][C:13]([S:18]([O:11][CH2:10][CH2:9][O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)(=[O:19])=[O:20])=[CH:14][CH:15]=1

Participants

5

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 8623o-Toluenesulfonyl chlorideHCID 121412-(Benzyloxy) ethanolHCID 24758Sodium hydride

Product 1

HCID 5613752-(Benzyloxy)ethyl 4-methylbenzenesulfonate

Procedure

The 2-benzyloxyalkyl p-toluenesulfonate used in step (a) may be prepared by conventional techniques from commercially available material. For example, a solution of 2-benzyloxyethanol and toluene sulfonyl chloride may be added to a slurry of sodium hydride in ethylene glycol dimethyl ether cooled (e.g. using an ice bath) under a nitrogen atmosphere. After the addition, the mixture is warmed and allowed to react at room temperature. Crude 2-benzyloxyethyl p-toluenesulfonate may be obtained from the reaction mixture by diluting the mixture with diethyl ether, filtering the diluted mixture through anhydrous magnesium sulfate, and concentrating the filtered product under vacuum.

Workup

  1. custommay be prepared by conventional techniques from commercially available material
  2. temperaturecooled (e.g. using an ice bath) under a nitrogen atmosphere
  3. additionAfter the addition
  4. temperaturethe mixture is warmed
  5. customto react at room temperature

Sources & evidence

ORD record
ord-fa2af4bd651c4465a54920f6e3a7b62f
Source dataset
uspto-grants-1993_11
Patent number
US05266722

Reaction notes

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