Formic Acid → HCID 21459440, compound

HRID 1941033Notes

Reaction equation

HRID 1941033 reaction equation
C1O[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=3)[CH:7](C3CCCCC=3)[CH2:6]2)OC1C.C(OCC)(=O)C.[CH2:32]([OH:34])[CH3:33].C(O)=O.[C:38]1(C)[CH:43]=CC=[CH:40][CH:39]=1>[Ni].O>[F:17][C:15]1[CH:16]=[C:11]([CH:8]2[CH2:9][CH2:10][CH:5]([CH:33]3[CH2:40][CH2:39][CH2:38][CH2:43][C:32]3=[O:34])[CH2:6][CH2:7]2)[CH:12]=[C:13]([F:18])[CH:14]=1

Participants

8

Reactant 5

HCID 284Formic AcidHCID 702EthanolHCID 1140TolueneHCID 8857Ethyl AcetateHCID 86751778HCID 86751778, compound

Product 1

HCID 21459440HCID 21459440, compoundYield 59.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

The above 4-(3,5-difluorophenyl)-3-cyclohexenyl-1-cyclohexanone propyleneketal (114 g, 327 mmol) was hydrogenated in a mixed solvent of ethyl acetate with ethanol in the presence of Raney Ni catalyst (44.8 g), followed by filtering off the catalyst, distilling off the solvent under reduced pressure, adding to the residue, formic acid (50.0 g, 1.09 mol) and toluene (300 ml), refluxing the mixture for 4 hours, adding water to the reaction solution, washing the organic layer successively with a saturated aqueous solution of sodium bicarbonate and water, drying over magnesium sulfate, distilling off toluene under reduced pressure, and purifying the residue according to column chromatography treatment using toluene as a developing solvent, on silica gel, to obtain 4-(3,5-difluorophenyl)cyclohexyl-1-cyclohexanone (56.8 g, 194 mmol). Yield: 59.3%.

Workup

  1. filtrationby filtering off the catalyst
  2. distillationdistilling off the solvent under reduced pressure
  3. temperaturerefluxing the mixture for 4 hours
  4. washwashing the organic layer successively with a saturated aqueous solution of sodium bicarbonate and water
  5. dry with materialdrying over magnesium sulfate
  6. distillationdistilling off toluene under reduced pressure
  7. custompurifying the residue

Sources & evidence

ORD record
ord-dec606fe44814317bac7636c6f33003c
Source dataset
uspto-grants-1997_12
Patent number
US05702641

Reaction notes

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