Ethylene Glycol → Ethyl 2-(2-ethyl-1,3-dioxolan-2-yl)acetate

HRID 31654

Reaction equation

HRID 31654 reaction equation
[O:1]=[C:2]([CH2:9][CH3:10])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:11](O)[CH2:12][OH:13].C(OCC)(OCC)OCC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(OCC)(=O)C.CCCCCCC>[CH2:7]([O:6][C:4](=[O:5])[CH2:3][C:2]1([CH2:9][CH3:10])[O:13][CH2:12][CH2:11][O:1]1)[CH3:8]

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 31214Ethyl orthoformateHCID 78656Ethyl 3-oxovalerateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 14244230Ethyl 2-(2-ethyl-1,3-dioxolan-2-yl)acetateYield 58.9%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolvent

Procedure

A mixture of ethyl 3-oxopentanoate (5 g, 34.7 mmol), ethylene glycol (10.8 g, 174 mmol), triethyl orthoformate (5.14 g, 34.7 mmol), and p-toluenesulfonic acid monohydrate (598 mg, 3.14 mmol) was stirred at room temperature overnight. To the reaction mixture, heptane and ethyl acetate were added to dilute solution, which was washed with water. The organic layer was washed with a saturated saline solution, dried over magnesium sulfate, filtrated and the filtrate was concentrated under reduced pressure. The residue was dissolved in heptane and subjected to NH silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=1/0→10/1) to obtain the title compound (3.85 g, yield: 58.9%) as colorless oil.

Workup

  1. washwas washed with water
  2. washThe organic layer was washed with a saturated saline solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltrated
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in heptane
  7. washsubjected to NH silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=1/0→10/1)

Sources & evidence

ORD record
ord-0f477811c9694e35a09ec124018f0987
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Linked notes

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