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

HRID 1021005

Reaktionsgleichung

Reaktionsgleichung von HRID 1021005
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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21877217Toluene methylene chlorideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-d8d69f21d68e4417a51945fb50233f1c
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716513B2

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