Ethylene Glycol → 1,4,8-Trioxaspiro[4.5]decane

HRID 2359357Notes

Reaction equation

HRID 2359357 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:7]([OH:10])[CH2:8][OH:9].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1C=CC=CC=1>[O:9]1[C:4]2([CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[O:10][CH2:7][CH2:8]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 8894TetrahydropyranHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 534405191,4,8-Trioxaspiro[4.5]decaneYield 90.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Tetrahydro-4H-pyran (6.00 g, 60.0 mmol) was dissolved in benzene (120 mL), to which ethylene glycol (11.2 g, 180 mmol) and p-toluenesulfonic acid monohydrate (1.14 g, 6.00 mmol) were added. Using a Dean-Stark tube, the resulting mixture was refluxed for two hours while removing water generated. To the resulting reaction liquid, a saturated aqueous solution of sodium bicarbonate was added, followed by extraction with ethyl acetate. The resulting organic layer was washed with saturated brine, and dried over sodium sulfate. The solvent was distilled off under reduced pressure. The residue thus obtained was purified by basic silica gel column chromatography (hexane:ethyl acetate, 100:0-0:100, V/V) to give the desired title compound (7.79 g, yield 90%).

Workup

  1. additionwere added
  2. temperaturethe resulting mixture was refluxed for two hours
  3. customwhile removing water
  4. customTo the resulting reaction liquid
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe resulting organic layer was washed with saturated brine
  7. dry with materialdried over sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customThe residue thus obtained
  10. customwas purified by basic silica gel column chromatography (hexane:ethyl acetate, 100:0-0:100, V/V)

Sources & evidence

ORD record
ord-8b80f94449e743d9a586de6d7cfe7135
Source dataset
uspto-grants-2014_04
Patent number
US08685981B2

Reaction notes

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