Reaction #2487415

Reaction equation

2-Hydroxyethyl methacrylate

succinic anhydride

Triethylamine

→

liquid

Yield 77.8%

4-(2-(Methacryloyloxy)ethoxy)-4-oxobutanoic Acid

Yield 77.8%

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   Temperaturethe reaction mixture was refluxed for 1.5 hours
2. 2
   Washwashed with 2 M HCl (150 mL)
3. 3
   OtherThe organic phase was separated from the aqueous phase
4. 4
   Dryingdried (MgSO4 and Na2SO4)
5. 5
   Otherevaporated to dryness

Procedure

2-Hydroxyethyl methacrylate (25 g, 0.195 mol) and succinic anhydride (19.5 g, 0.195 mol) were added to dichloromethane (200 mL) under nitrogen. Triethylamine (28.5 ml, 20.72 g, 1.05 equiv.) was then added dropwise over 20 minutes and the reaction mixture was refluxed for 1.5 hours. The reaction mixture was then diluted with dichloromethane (200 mL), washed with 2 M HCl (150 mL) and then finally with brine (100 mL). The organic phase was separated from the aqueous phase, dried (MgSO4 and Na2SO4) and evaporated to dryness, yielding a viscous, colourless liquid (34.9 g, 77.8% yield). 1H NMR δ 1.89 (s, 3H, CH3), 2.59-2.67 (m, 4H, 2×CH2CO), 4.31 (br. s, 4H, 2×CH2OCO), 5.55 (s, 1H, vinyl CH), 6.08 (s, 1H, vinyl CH). 13C NMR δ 17.96, 28.64, 28.73, 62.15, 62.29, 126.12, 135.79, 167.11, 171.90, 177.73.

Source