Ethanol → 2-Ethoxalyloxyethyl methacrylate

HRID 6403

Reaktionsgleichung

Reaktionsgleichung von HRID 6403
[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.C1(C=CC(O)=CC=1)O>[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 76,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 785HydroquinoneKatalysatorHCID 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 hydroquinone (polymerization inhibitor) were added. The mixture was heated to keep 120° C. for 4 hours in nitrogen atmosphere with distilling 14 ml (0.25 mol) of ethanol away. The reaction mixture was evaporated to remove excess diethyl oxalate and then distilled under vacuum to obtain 88.1 g (yield 76.5%) of 2-ethoxalyloxyethyl methacrylate (colorless transparent liquid) (bp 98° 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-f3ba761238a143e1b68d0ab2aac52f4d
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05248749

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