Reaction #6502

Reaction equation

2-hydroxyethyl methacrylate

diethyl oxalate

ethanol

→

2-ethoxalyloxyethyl methacrylate

Yield 73.2%

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
   Otherat about 120° C.
5. 5
   Otherfor 2 hours
6. 6
   OtherThe reaction mixture was evaporated
7. 7
   Otherto remove excess diethyl oxalate
8. 8
   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 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).

Source