Dimethyl Sulfate → Phenyldimethylsulfonium methylsulfate

HRID 652307Notes

Reaction equation

HRID 652307 reaction equation
[C:1]1([S:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:9][O:10][S:11]([O:14]C)(=[O:13])=[O:12]>>[CH3:9][O:10][S:11]([O-:14])(=[O:13])=[O:12].[C:1]1([S+:7]([CH3:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 6497Dimethyl SulfateHCID 7520Thioanisole

Product 1

HCID 21201015Phenyldimethylsulfonium methylsulfate

Procedure

To 24.8 g of thioanisole heated to 90° C., 27.8 g of (0.22 mole) of dimethylsulfate was added dropwise with stirring over 30 minutes, while maintaining its temperature at 90°-95° C. Stirring of the mixture at the same temperature for 30 minutes resulted in quantitative formation of phenyldimethylsulfonium methylsulfate (sulfonium salt) which formed a solid mass at room temperature. The solid mass was dissolved in 110 ml of hot dichloromethane, then cooled to 0° C. with stirring to afford a suspended solution of the sulfonium salt which was employed in the following reaction.

Workup

  1. temperaturewhile maintaining its temperature at 90°-95° C
  2. stirringStirring of the mixture at the same temperature for 30 minutes

Sources & evidence

ORD record
ord-3bbb8c9758514e0bafa7045abdf7b862
Source dataset
uspto-grants-1987_06
Patent number
US04670607

Reaction notes

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