Ethylene Glycol → HCID 57485780, compound

HRID 749124Notes

Reaction equation

HRID 749124 reaction equation
[O:1]=[C:2]1[CH2:7][CH:6]([C:8]([O:10][CH3:11])=[O:9])[CH2:5][CH:4]([C:12]([O:14][CH3:15])=[O:13])[CH2:3]1.[CH2:16](O)[CH2:17][OH:18]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:18]1[C:2]2([CH2:3][CH:4]([C:12]([O:14][CH3:15])=[O:13])[CH2:5][CH:6]([C:8]([O:10][CH3:11])=[O:9])[CH2:7]2)[O:1][CH2:16][CH2:17]1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 13028458Dimethyl 5-oxocyclohexane-1,3-dicarboxylate

Product 1

HCID 57485780HCID 57485780, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

To a solution of dimethyl 5-oxocyclohexane-1,3-dicarboxylate (6.0 g, 28 mmol) in toluene (50 ml) was added ethylene glycol (3.73 g, 56.6 mmol) and p-toluenesulfonic acid (65 mg). The reaction was refluxed overnight, using a Dean-Stark trap to remove the excess water. The reaction was worked up by removing the toluene by rotary evaporation, adding brine (10 ml) and extracting with ethyl acetate (3×40 ml). The combined extracts were dried over sodium sulfate, filtered and concentrated by rotary evaporation to give the desired product as a thick colorless liquid (6.0 g, 82%).

Workup

  1. temperatureThe reaction was refluxed overnight
  2. customto remove the excess water
  3. customby removing the toluene
  4. customby rotary evaporation
  5. additionadding brine (10 ml)
  6. extractionextracting with ethyl acetate (3×40 ml)
  7. dry with materialThe combined extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-e5eae5eb83de418d9787894a6df022e0
Source dataset
uspto-grants-2008_07
Patent number
US07402592B2

Reaction notes

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