Ethylene Glycol → HCID 12842291, compound

HRID 1976741Notes

Reaction equation

HRID 1976741 reaction equation
[C:1]1([S:7]([CH:10]2[CH2:15][CH2:14][CH2:13][C:12](=[O:16])[CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:17](O)[CH2:18][OH:19].C(=O)(O)[O-].[Na+]>C1C=CC=CC=1>[CH2:17]1[CH2:18][O:19][C:12]2([CH2:13][CH2:14][CH2:15][CH:10]([S:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)(=[O:8])=[O:9])[CH2:11]2)[O:16]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 516892Sodium BicarbonateHCID 12842290HCID 12842290, compound

Product 1

HCID 12842291HCID 12842291, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 5.3 g of 3-(phenylsulfonyl)-cyclohexan-1-one in 60 ml of benzene, were added 0.3 ml of 1,2-ethanediol and 0.2 g of anhydrous paratoluenesulfonic acid. The reaction mixture was heated under reflux for 4 hours. After the reaction, a 2M aqueous sodium bicarbonate solution was added and the resulting mixture was extracted with ethyl acetate three times. The combined organic layers were washed with saturated saline and then, dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was recrystallized from ethyl ether, whereby 6.1 g of 1,1-(ethylenedioxy)-3-(phenylsulfonyl)-cyclohexane were obtained in the form of white crystals. Yield: 97%

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 4 hours
  3. customAfter the reaction
  4. extractionthe resulting mixture was extracted with ethyl acetate three times
  5. washThe combined organic layers were washed with saturated saline
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThe residue was recrystallized from ethyl ether

Sources & evidence

ORD record
ord-96d87701c77049e4a110de41b8543490
Source dataset
uspto-grants-2001_05
Patent number
US06228893B1

Reaction notes

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