Ethylene Glycol → HCID 21999137, compound

HRID 1976752Notes

Reaction equation

HRID 1976752 reaction equation
[CH3:1][CH:2]1[CH:7]([S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH2:6][CH2:5][CH2:4][C:3]1=[O:17].[CH2:18](O)[CH2:19][OH:20].C(=O)(O)[O-].[Na+]>C1C=CC=CC=1>[CH2:18]1[CH2:19][O:20][C:3]2([CH2:4][CH2:5][CH2:6][CH:7]([S:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)(=[O:10])=[O:9])[CH:2]2[CH3:1])[O:17]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 516892Sodium BicarbonateHCID 21999124HCID 21999124, compound

Product 1

HCID 21999137HCID 21999137, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution obtained by dissolving 1.4 g of 2-methyl-3-(phenylsulfonyl)-cyclohexan-1-one in 20 ml of benzene, were added 0.41 ml of 1,2-ethanediol and 0.1 g of anhydrous paratoluenesulfonic acid. The resulting 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 dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was recrystallized from ethyl ether, whereby 1,1-(ethylenedioxy)-2-methyl-3-(phenylsulfonyl)-cyclohexane was obtained in the form of white crystals. Yield: 95%

Workup

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

Sources & evidence

ORD record
ord-14d096212c99488faf173d33f022c79b
Source dataset
uspto-grants-2001_05
Patent number
US06228893B1

Reaction notes

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