Ethylene Glycol → HCID 21999127, compound

HRID 1976749Notes

Reaction equation

HRID 1976749 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 nm of 1,2-ethanediol and 0.3 g of anhydrous paratoluenesulfonic acid. The resulting mixture was heated under ref lux 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, 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%

Workup

  1. customTo a solution obtained
  2. temperatureThe resulting mixture was heated under ref lux 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. customfollowed by recrystallization from ethyl ether

Sources & evidence

ORD record
ord-0089e21cc5ea4890b7dfaa200ebd30b0
Source dataset
uspto-grants-2001_05
Patent number
US06228893B1

Reaction notes

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