Ethylene Glycol → 1,2-Ethanediol, 1,2-dimethanesulfonate

HRID 1021005

Reaction equation

HRID 1021005 reaction equation
C(=O)([O-])[O-].[K+].[K+].C(N(C(C)C)CC)(C)C.[CH2:16]([OH:19])[CH2:17][OH:18].[CH3:20][S:21](Cl)(=[O:23])=[O:22]>ClCCl.C1(C)C=CC=CC=1>[CH3:20][S:21]([O:18][CH2:17][CH2:16][O:19][S:21]([CH3:20])(=[O:23])=[O:22])(=[O:23])=[O:22]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 207961,2-Ethanediol, 1,2-dimethanesulfonate

Reagents, catalysts & solvents 1

HCID 21877217Toluene methylene chlorideSolvent

Procedure

Potassium carbonate (6.7 g, 48.5 mmol) and diisopropylethylamine (0.3 g, 2.3 mmol) were suspended in dichloromethane-toluene (1/1, 10 mL), and ethylene glycol (1.5 g, 23.3 mmol) and methanesulfonyl chloride (5.5 g, 48.0 mmol) were dropped at the same time in an ice bath. A reaction was effected at room temperature for 3 hours and, thereafter, the reaction was terminated by addition to ice water. An organic layer separated through liquid separation was concentrated, so as to obtain the desired product, 1,2-bis(methanesulfonyloxy)ethane, at a yield of 36% (1.8 g, 8.4 mmol). The measurement result of 1H NMR is as described below.

Workup

  1. customthe reaction was terminated by addition to ice water
  2. customAn organic layer separated through liquid separation
  3. concentrationwas concentrated

Sources & evidence

ORD record
ord-d8d69f21d68e4417a51945fb50233f1c
Source dataset
uspto-grants-2014_05
Patent number
US08716513B2

Linked notes

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