Diethyl Oxalate → 2-Ethoxalyloxyethyl methacrylate

HRID 1756868Notes

Reaction equation

HRID 1756868 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]>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]

Participants

5

Reactant 2

HCID 7268Diethyl OxalateHCID 133602-Hydroxyethyl Methacrylate

Product 1

HCID 194284412-Ethoxalyloxyethyl methacrylateYield 56.3%

Reagents, catalysts & solvents 2

HCID 23742,5-Di-tert-butylhydroquinoneCatalystHCID 6101p-Toluenesulfonic acidCatalyst

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 2,5-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).

Workup

  1. customA 500 ml flask equipped with a decanter
  2. additionwere added
  3. temperatureThe mixture was heated
  4. distillationatmosphere with distilling 23.5 ml (0.40. mol) of ethanol away
  5. customThe reaction mixture was evaporated
  6. customto remove excess diethyl oxalate
  7. distillationdistilled under vacuum

Sources & evidence

ORD record
ord-549bfdefab1e428f91b5d8f6dc90afd7
Source dataset
uspto-grants-1995_08
Patent number
US05442096

Reaction notes

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