Ethylene Glycol → HCID 22394927, compound

HRID 1375122Notes

Reaction equation

HRID 1375122 reaction equation
[CH3:1][CH:2]1[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].[CH2:18](O)[CH2:19][OH:20].C(=O)(O)[O-].[Na+]>C1C=CC=CC=1>[CH2:18]1[CH2:19][O:20][C:5]2([CH2:6][CH2:7][CH:2]([CH3:1])[CH:3]([S:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)(=[O:10])=[O:11])[CH2:4]2)[O:8]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 516892Sodium BicarbonateHCID 223949304-Methyl-3-(phenylsulfonyl)-cyclohexan-1-one

Product 1

HCID 22394927HCID 22394927, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 2.45 g of 4-methyl-3-(phenylsulfonyl)-cyclohexan-1-one in 40 ml of benzene, were added 0.7 ml of 1,2-ethanediol and 0.2 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 then distilled off under reduced pressure. The residue was recrystallized from ethyl ether, whereby 1,1-(ethylenedioxy)-4-methyl-3-(phenylsulfonyl)-cyclohexane was obtained in the form of white crystals. Yield: 97%, Melting point: 105 to 106° C.

Workup

  1. temperatureThe resulting 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 then distilled off under reduced pressure
  8. customThe residue was recrystallized from ethyl ether

Sources & evidence

ORD record
ord-cc9633e2e1ac41dc8a7fa14151867efc
Source dataset
uspto-grants-2007_01
Patent number
US07166642B1

Reaction notes

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