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Ethanol → 2-Ethoxalyloxyethyl methacrylate

HRID 6403
Notes
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Reaction equation

HRID 6403 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.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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 702EthanolHCID 7268Diethyl OxalateHCID 133602-Hydroxyethyl Methacrylate

Product 1

HCID 194284412-Ethoxalyloxyethyl methacrylateYield 76.5%

Reagents, catalysts & solvents 2

HCID 785HydroquinoneCatalystHCID 6101
p-Toluenesulfonic acid
Catalyst

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 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).

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-f3ba761238a143e1b68d0ab2aac52f4d
Source dataset
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05248749

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes