Reaction #6499

Reaction equation

2-hydroxyethyl methacrylate

diethyl oxalate

ethanol

→

2-ethoxalyloxyethyl methacrylate

Yield 76.5%

Conditions

Workup

1. 1
   OtherA 500 ml flask equipped with a decanter
2. 2
   workup.ADDITIONwere added
3. 3
   TemperatureThe mixture was heated
4. 4
   OtherThe reaction mixture was evaporated
5. 5
   Otherto remove excess diethyl oxalate
6. 6
   workup.DISTILLATIONdistilled under vacuum

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).

Source