4-(2,3-Difluorophenyl)-3-cyclohexenone ethylene ketal → 4-(2,3-Difluorophenyl)cyclohexanone

HRID 726490Notes

Reaction equation

HRID 726490 reaction equation
C1O[C:4]2([CH2:9][CH2:8][C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:11]=3[F:17])=[CH:6][CH2:5]2)[O:3]C1>C(OCC)(=O)C>[F:17][C:11]1[C:12]([F:16])=[CH:13][CH:14]=[CH:15][C:10]=1[CH:7]1[CH2:6][CH2:5][C:4](=[O:3])[CH2:9][CH2:8]1

Participants

3

Reactant 1

HCID 539656924-(2,3-Difluorophenyl)-3-cyclohexenone ethylene ketal

Product 1

HCID 189208724-(2,3-Difluorophenyl)cyclohexanoneYield 72%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

First, 39.4 g of 4-(2,3-difluorophenyl)-3-cyclohexenone ethylene ketal, 150 ml of ethyl acetate, and 1.0 g of 10% palladium catalyst(Pd-C) were placed in a 500 ml autoclave. The mixture was stirred at room temperature for 43 hours under a hydrogen pressure of 10 kg/cm2. A catalyst was filtered away and a filtrate was concentrated. Thereafter, 225 ml of 1,4-dioxane, 675 ml of water, and 1 g of p-toluenesulfonic acid monohydrate were added to the residue. The mixture was stirred under reflux for 2 hours. The reaction mixture was extracted with ether. The ether layer was washed with water and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away. The residue was purified by silica gel column chromatography (eluent: toluene/hexane=19:1) and distilled under reduced pressure to obtain 17.5 g of 4-(2,3-difluorophenyl)cyclohexanone (Y: 72%). The compound thus obtained had a purity of 98.9% by GC and a b.p. of 125° C. to 128° C./0.6 mmHg.

Workup

  1. filtrationA catalyst was filtered away
  2. concentrationa filtrate was concentrated
  3. additionThereafter, 225 ml of 1,4-dioxane, 675 ml of water, and 1 g of p-toluenesulfonic acid monohydrate were added to the residue
  4. stirringThe mixture was stirred
  5. temperatureunder reflux for 2 hours
  6. extractionThe reaction mixture was extracted with ether
  7. washThe ether layer was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThereafter, the solvent was distilled away
  10. customThe residue was purified by silica gel column chromatography (eluent: toluene/hexane=19:1)
  11. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-11c99184a5d64869bde32aae8355ee84
Source dataset
uspto-grants-1998_01
Patent number
US05709911

Reaction notes

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