Dichloromethane → 2-Isopropoxyethyl Methanesulfonate

HRID 41233

Reaction equation

HRID 41233 reaction equation
ClCCl.[CH:4]([O:7][CH2:8][CH2:9][OH:10])([CH3:6])[CH3:5].C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C(OCC)(=O)C.O>[CH3:18][S:19]([O:10][CH2:9][CH2:8][O:7][CH:4]([CH3:6])[CH3:5])(=[O:21])=[O:20]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 7996IsopropylethanediolHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 184650452-Isopropoxyethyl Methanesulfonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a dichloromethane (50 mL) mixture of 2-isopropoxyethanol (5.21 g, 50.0 mmol) and triethylamine (7.70 mL, 55.0 mmol), was added methanesulfonyl chloride (4.30 mL, 55.0 mmol) while stirring on ice, and the resulting mixture was stirred for 30 minutes. Water and ethyl acetate were added to the mixture. After the mixture was thoroughly shaken, the organic layer was separated, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was filtered, and the solvent in the filtrate was then distilled off under reduced pressure.

Workup

  1. stirringthe resulting mixture was stirred for 30 minutes
  2. stirringAfter the mixture was thoroughly shaken
  3. customthe organic layer was separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe mixture was filtered
  7. distillationthe solvent in the filtrate was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-2d7de98408074f379c8ba234f78ceff7
Source dataset
uspto-grants-2013_09
Patent number
US08530504B2

Linked notes

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