Succinic anhydride → (2-((2-Methyl-1-oxoallyl)oxy)ethyl) hydrogen succinate

HRID 1644134Notes

Reaction equation

HRID 1644134 reaction equation
[C:1]([O:6][CH2:7][CH2:8][OH:9])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:10]1(=[O:16])[O:15][C:13](=[O:14])[CH2:12][CH2:11]1.C(N(CC)CC)C>ClCCl>[C:1]([O:6][CH2:7][CH2:8][O:9][C:10](=[O:16])[CH2:11][CH2:12][C:13]([OH:15])=[O:14])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 133602-Hydroxyethyl Methacrylate

Product 1

HCID 88720(2-((2-Methyl-1-oxoallyl)oxy)ethyl) hydrogen succinateYield 77.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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 (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.

Workup

  1. temperaturethe reaction mixture was refluxed for 1.5 hours
  2. washwashed with 2 M HCl (150 mL)
  3. customThe organic phase was separated from the aqueous phase
  4. dry with materialdried (MgSO4 and Na2SO4)
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-5880d6a208d24895946dffd7d7c11a5e
Source dataset
uspto-grants-2012_02
Patent number
US08124188B2

Reaction notes

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