Ethanol → 2-Ethoxalyloxyethyl methacrylate

HRID 1681233Notes

Reaction equation

HRID 1681233 reaction equation
[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=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]

Participants

6

Reactant 3

HCID 702EthanolHCID 7268Diethyl OxalateHCID 133602-Hydroxyethyl Methacrylate

Product 1

HCID 194284412-Ethoxalyloxyethyl methacrylateYield 76.5%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 16043Tert-ButylhydroquinoneCatalyst

Procedure

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-t-butylhydroquinone (polymerization inhibitor) were added. The mixture was heated to keep about 130° C. for 3 hours in nitrogen atmosphere with distilling 22 ml (0.38 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 76.5%) of 2-ethoxalyloxyethyl methacrylate (bp 84°-125° C./0.4 mmHg).

Workup

  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

Sources & evidence

ORD record
ord-d8e2847b53454782b0f9441f8be50a70
Source dataset
uspto-grants-1992_12
Patent number
US05169896

Reaction notes

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