4-(3,5-Dichlorophenylmethylene)cyclohexanone → 4-(3,5-Dichlorophenylmethyl)cyclohexanol

HRID 1735297Notes

Reaction equation

HRID 1735297 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]2[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[H][H]>[Pd].C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]2[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 2

HCID 197052634-(3,5-Dichlorophenylmethylene)cyclohexanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 197052214-(3,5-Dichlorophenylmethyl)cyclohexanolYield 90.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 7.5 grams (0.031 mole) of 4-(3,5-dichlorophenylmethylene)cyclohexanone and 1.0 gram (catalyst) of 10% palladium on charcoal (Degussa type) in 100 mL of ethanol was placed in a hydrogenation bottle and hydrogenated using a Parr hydrogenation apparatus. Upon completion of 2 hours at 50 psi, the reaction had used 25% of the theoretical amount of hydrogen. After this time the reaction mixture was filtered, and an aliquot was concentrated under reduced pressure to a residue. An NMR spectrum indicated that complete hydrogenation had not taken place. The hydrogenation was again conducted using the cyclohexanone above, and 1.0 gram of fresh 10% palladium on charcoal in 100 mL of ethanol. Upon the uptake of the theoretical amount of hydrogen, the reaction mixture was filtered. The filtrate was allowed to stand about 60 hours and then was concentrated under reduced pressure, yielding 7.3 grams of 4-(3,5-dichlorophenylmethyl)cyclohexanol. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customUpon completion of 2 hours
  2. filtrationAfter this time the reaction mixture was filtered
  3. concentrationan aliquot was concentrated under reduced pressure to a residue
  4. filtrationUpon the uptake of the theoretical amount of hydrogen, the reaction mixture was filtered
  5. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-e455a5617d19401c84542245033f490b
Source dataset
uspto-grants-1996_07
Patent number
US05536725

Reaction notes

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