Ethanol → 2-Ethoxalyloxyethyl methacrylate

HRID 6406

Reaktionsgleichung

Reaktionsgleichung von HRID 6406
[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>C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC.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 73,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23742,5-Di-tert-butylhydroquinoneKatalysatorHCID 9809426Di-n-butyldilauryltinKatalysator

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 dibutyltin dilaurate (catalyst) and 4 g of 2,5-di-t-butylhydroquinone (polymerization inhibitor) were added. The mixture was heated to keep it at about 120° C. for 2 hours in nitrogen atmosphere with distilling 32.5 ml (0.56 mol) of ethanol away. The reaction mixture was evaporated to remove excess diethyl oxalate and then distilled under vacuum to obtain 84.2 g (yield 73.2%) of 2-ethoxalyloxyethyl methacrylate (bp 124° C./0.4 mmHg).

Aufarbeitung

  1. customA 500 ml flask equipped with a decanter
  2. additionwere added
  3. temperatureThe mixture was heated
  4. customat about 120° C.
  5. customfor 2 hours
  6. customThe reaction mixture was evaporated
  7. customto remove excess diethyl oxalate
  8. distillationdistilled under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1e1b570bc8ce444bb33a68c096a4880b
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05248749

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