Ethylene Glycol → Ethyl 2-(2-methyl-1,3-dioxolan-2-yl)butanoate

HRID 1024345

Reaction equation

HRID 1024345 reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH:4]([CH2:8][CH3:9])[C:5]([CH3:7])=[O:6].[CH2:11]([OH:14])[CH2:12]O.[CH3:15]C1C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH2:1]([O:2][C:3](=[O:10])[CH:4]([C:5]1([CH3:7])[O:14][CH2:11][CH2:12][O:6]1)[CH2:8][CH3:9])[CH3:15]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 103534Butanoic acid, 2-ethyl-3-oxo-, methyl esterHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 12948748Ethyl 2-(2-methyl-1,3-dioxolan-2-yl)butanoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl-2-ethylacetoacetate (100 mL) was taken up in toluene (250 mL). Ethylene glycol (46.9 mL, 1.35 equiv.) and a catalytic amount of p-TsOH.H2O were added, and the mixture was refluxed overnight under Dean-Stark conditions. After cooling to ambient temperature, the mixture was washed with 5% aqueous NaHCO3 and saturated aqueous NaCl, the organic phase was dried over Na2SO4 and evaporated under reduced pressure. The residue was purified by repeated vacuum distillation (118-128° C., 15 mbar), yielding 85.5 g of product. 1H NMR (400 MHz, CDCl3) δ 0.90 (t, J=7 Hz, 3H), 1.28 (t, J=7 Hz, 3H), 1.40 (s, 3H), 1.59-1.83 (m, 2H), 2.56 (dd, J=11.5 and 4 Hz, 1H), 3.90-4.06 (m, 4H), 4.18 (m, 2H).

Workup

  1. temperaturethe mixture was refluxed overnight under Dean-Stark conditions
  2. washthe mixture was washed with 5% aqueous NaHCO3 and saturated aqueous NaCl
  3. dry with materialthe organic phase was dried over Na2SO4
  4. customevaporated under reduced pressure
  5. distillationThe residue was purified by repeated vacuum distillation (118-128° C., 15 mbar)

Sources & evidence

ORD record
ord-3524af23d3594868b08969d5f4ba1113
Source dataset
uspto-grants-2014_05
Patent number
US08722887B2

Linked notes

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