Ethanol → 2-Ethoxalyloxyethyl methacrylate

HRID 6405

Reaktionsgleichung

Reaktionsgleichung von HRID 6405
[C:1]([O:6][CH2:7][CH2:8][OH:9])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:10](OCC)(=[O:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12].C(O)C>C1(C)C=CC(S(O)(=O)=O)=CC=1.C(C1C=C(O)C(C(C)(C)C)=CC=1O)(C)(C)C>[C:1]([O:6][CH2:7][CH2:8][O:9][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:16])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Komponenten

6

Edukt 3

HCID 702EthanolHCID 7268Diethyl OxalateHCID 133602-Hydroxyethyl Methacrylate

Produkt 1

HCID 194284412-Ethoxalyloxyethyl methacrylateAusbeute 56,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23742,5-Di-tert-butylhydroquinoneKatalysatorHCID 6101p-Toluenesulfonic acidKatalysator

Versuchsvorschrift

A 500 ml flask equipped with a decanter, a thermometer, a stirrer and an inlet for nitrogen gas was charged with 65.1 g (0.5 mol) of 2-hydroxyethyl methacrylate and 365.4 g (2.5 mol) of diethyl oxalate, to which 2 g (10 mmol) of p-toluenesulfonic acid (catalyst) and 4 g of 2,5-di-t-butylhydroquinone (polymerization inhibitor) were added. The mixture was heated to keep about 130° C. for 3 hours in nitrogen atmosphere with distilling 23.5 ml (0.40 mol) of ethanol away. The reaction mixture was evaporated to remove excess diethyl oxalate and then distilled under vacuum to obtain 64.8 g (yield 52.4%) of 2-ethoxalyloxyethyl methacrylate (bp 95°-125° C./0.3 mmHg).

Aufarbeitung

  1. customA 500 ml flask equipped with a decanter
  2. additionwere added
  3. temperatureThe mixture was heated
  4. customThe reaction mixture was evaporated
  5. customto remove excess diethyl oxalate
  6. distillationdistilled under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-55437dbf90b64b46927be1c1700be2ac
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05248749

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