Ethylene Glycol → HCID 70957905, compound

HRID 337818Notes

Reaction equation

HRID 337818 reaction equation
[I:1][C:2]1[C:3](=[O:10])[CH2:4][CH2:5][C:6]([CH3:9])([CH3:8])[CH:7]=1.[CH2:11](O)[CH2:12][OH:13]>C1C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[I:1][C:2]1[C:3]2([CH2:4][CH2:5][C:6]([CH3:9])([CH3:8])[CH:7]=1)[O:13][CH2:12][CH2:11][O:10]2

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 9992273HCID 9992273, compound

Product 1

HCID 70957905HCID 70957905, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 241BenzeneSolvent

Procedure

A solution of 2-iodo-4,4-dimethylcyclohex-2-en-1-one (Synlett, 2005, 1263-1266; 5.46 g, 21.8 mmol), ethylene glycol (3.00 g, 48.3 mmol), p-toluenesulfonic acid hydrate (100 mg) in benzene (100 mL) was stirred for 7 hours under reflux, and the solvent was subjected to azeotropic distillation with water. After allowing to cool, a saturated aqueous solution of sodium hydrogencarbonate (100 mL) was added to the reaction solution, and an organic layer was extracted. The thus obtained organic layer was dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography (hexane/ethyl acetate=95:5) to yield the title compound (5.78 g, 90%) as a colorless oil.

Workup

  1. temperatureunder reflux
  2. distillationthe solvent was subjected to azeotropic distillation with water
  3. temperatureto cool
  4. additiona saturated aqueous solution of sodium hydrogencarbonate (100 mL) was added to the reaction solution
  5. extractionan organic layer was extracted
  6. dry with materialThe thus obtained organic layer was dried over anhydrous sodium sulfate
  7. concentrationAfter vacuum concentration
  8. customthe residue was purified with silica gel chromatography (hexane/ethyl acetate=95:5)

Sources & evidence

ORD record
ord-ed1c234cc1c448bfb8f96c02c603b7f3
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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