Water → 2-Methoxyethyl methanesulfonate

HRID 1628127Notes

Reaction equation

HRID 1628127 reaction equation
CN1C=CN=C1.[CH3:7][S:8](Cl)(=[O:10])=[O:9].[CH3:12][O:13][CH2:14][CH2:15][OH:16].O>ClCCl>[CH3:7][S:8]([O:16][CH2:15][CH2:14][O:13][CH3:12])(=[O:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 13901-MethylimidazoleHCID 80192-MethoxyethanolHCID 31297Methanesulfonyl chloride

Product 1

HCID 1462932-Methoxyethyl methanesulfonateYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Methylimidazole (50 g) and methanesulfonyl chloride (66 g) were mixed in dichloromethane in a 500 mL two-bulb flask. After adding ethylene glycol monomethyl ether (42 g) dropwise at 10° C., the mixture was stirred at room temperature for 4 hours. After the reaction was completed, water was added. After stirring for 10 minutes, the solvent layer in which the product was dissolved was separated from the aqueous layer in which the byproduct was dissolved. The product was yielded by removing the solvent at room temperature using an evaporator (yield: 98%), and the byproduct 1-methylimidazolium chloride was recovered as 1-methylimidazole using 40 wt % NaOH aqueous solution and used again (yield: 95%).

Workup

  1. stirringAfter stirring for 10 minutes
  2. dissolutionthe solvent layer in which the product was dissolved
  3. customwas separated from the aqueous layer in which the byproduct
  4. dissolutionwas dissolved
  5. customThe product was yielded
  6. customby removing the solvent at room temperature
  7. customan evaporator (yield: 98%)
  8. customthe byproduct 1-methylimidazolium chloride was recovered as 1-methylimidazole using 40 wt % NaOH aqueous solution

Sources & evidence

ORD record
ord-5736e31c88a1457ab91054a288cb1c69
Source dataset
uspto-grants-2014_07
Patent number
US08785711B2

Reaction notes

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