Ethylene Glycol → HCID 22394927, compound

HRID 1175054Notes

Reaction equation

HRID 1175054 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, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 2.45 g of 4-methyl-3-(phenylsulfonyl)-cyclohexan-1-one dissolved in 40 ml of benzene, were added 0.7 ml of 1,2-ethanediol and 0.2 g of paratoluenesulfonic anhydride. 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 ether, whereby 1,1-(ethylenedioxy)-4-methyl-3-(phenylsulfonyl)-cyclohexane was obtained in the form of white crystals (yield: 97%).

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 ether

Sources & evidence

ORD record
ord-29e15807ec64479eacd8929a22bb2719
Source dataset
uspto-grants-2010_11
Patent number
US07838565B2

Reaction notes

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