Ethylene Glycol → HCID 21999127, compound

HRID 1375126Notes

Reaction equation

HRID 1375126 reaction equation
[CH3:1][C:2]1([CH3:18])[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH:3]1[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:11])=[O:10].[CH2:19](O)[CH2:20][OH:21].C(=O)(O)[O-].[Na+]>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:18])[CH2:7][CH2:6][C:5]2([O:21][CH2:20][CH2:19][O:8]2)[CH2:4][CH:3]1[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:10])=[O:11]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 516892Sodium BicarbonateHCID 219991254,4-Dimethyl-3-(phenylsulfonyl)-cyclohexan-1-one

Product 1

HCID 21999127HCID 21999127, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution obtained by dissolving 4.4 g of 4,4-dimethyl-3-(phenylsulfonyl)-cyclohexan-1-one in 45 ml of benzene, were added 1.1 ml of 1,2-ethanediol and 0.3 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 saturatd saline and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, followed by recrystallization from ethyl ether, whereby 4,4-dimethyl-1,1 (ethylenedioxy)-3-(phenylsulfonyl)-cyclohexane was obtained in the form of white crystals. Yield: 84%, Melting point: 113 to 115° C.

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 saturatd saline
  7. dry with materialdried over magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customfollowed by recrystallization from ethyl ether

Sources & evidence

ORD record
ord-d870290062ed4c3a92b79c39381a9238
Source dataset
uspto-grants-2007_01
Patent number
US07166642B1

Reaction notes

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