p-Toluenesulfonic acid → HCID 19706374, compound

HRID 726502Notes

Reaction equation

HRID 726502 reaction equation
C1O[C:4]2([CH2:9][CH2:8][CH:7]([CH:10]3[CH2:15][CH2:14][C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:17]=4[F:23])=[CH:12][CH2:11]3)[CH2:6][CH2:5]2)[O:3]C1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O1CCOCC1>O>[F:23][C:17]1[C:18]([F:22])=[CH:19][CH:20]=[CH:21][C:16]=1[C:13]1[CH2:14][CH2:15][CH:10]([CH:7]2[CH2:6][CH2:5][C:4](=[O:3])[CH2:9][CH2:8]2)[CH2:11][CH:12]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 312751,4-DioxaneHCID 57598852HCID 57598852, compound

Product 1

HCID 19706374HCID 19706374, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

First, 8 g of 4-[4-(2,3-difluorophenyl)-3-cyclohexenyl]cyclohexanone ethylene ketal, 0.5 g of p-toluenesufonic acid, 40 ml of dioxane, and 110 ml of water were placed in a 300 ml flask. The mixture was stirred under reflux for 5 hours. The reaction mixture was extracted with ether. The ether layer was washed with water and dried over anhydrous sodium sulfate. Then, the solvent was distilled away. The residue was recrystallized from hexane to obtain 5.65 g of 4-[4-(2,3-difluorophenyl)-3-cyclohexenyl]cyclohexanone (Y: 81.4%). The compound thus obtained had a purity of 98.4% by GC.

Workup

  1. temperatureunder reflux for 5 hours
  2. extractionThe reaction mixture was extracted with ether
  3. washThe ether layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThen, the solvent was distilled away
  6. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-93cb7b37535b4f13b9c909054ea17c90
Source dataset
uspto-grants-1998_01
Patent number
US05709911

Reaction notes

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