Ethylene Glycol → 1,4-Dioxaspiro(4.5)decane

HRID 2200577Notes

Reaction equation

HRID 2200577 reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.II.[CH2:10](O)[CH2:11][OH:12]>C(OCC)(=O)C>[O:7]1[C:1]2([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[O:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 807IodineHCID 7967Cyclohexanone

Product 1

HCID 90931,4-Dioxaspiro(4.5)decaneYield 46.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of cyclohexanone (10 g, 0.102 mol) in ethylene glycol (50 mL) was added iodine (3.88 g, 15.3 mmol) and the resulting mixture was stirred at room temperature overnight. The mixture was diluted with ethyl acetate and extracted with saturated aqueous sodium thiosulfate. The organic phase was dried and concentrated to give a crude product, which was purified via silica gel chromatography eluting with ethyl acetate/petroleum ether (1:8) to give 1,4-dioxaspiro[4.5]decane (6.8 g, 46.9% yield) as light oil. 1H-NMR (CDCl3) δ 3.93(s, 4H), 1.58-1.59 (d, 8H), 1.39-1.41(m, 2H).

Workup

  1. extractionextracted with saturated aqueous sodium thiosulfate
  2. customThe organic phase was dried
  3. concentrationconcentrated
  4. customto give a crude product, which
  5. customwas purified via silica gel chromatography
  6. washeluting with ethyl acetate/petroleum ether (1:8)

Sources & evidence

ORD record
ord-75ef5fd243c7490582421b0d0ac712f1
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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