Acetone → 4-(2-Chloro-4-biphenylyl)-2-pentanone

HRID 1605658Notes

Reaction equation

HRID 1605658 reaction equation
[H][H].[BH4-].[Na+].CC(C)=O.[Cl:9][C:10]1[CH:15]=[C:14](/[C:16](/[CH3:21])=[CH:17]/[C:18](=[O:20])[CH3:19])[CH:13]=[CH:12][C:11]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)C.O.O.O.O.C([O-])(=O)C.[Ni+2].C([O-])(=O)C.B#[Ni]>[Cl:9][C:10]1[CH:15]=[C:14]([CH:16]([CH3:21])[CH2:17][C:18](=[O:20])[CH3:19])[CH:13]=[CH:12][C:11]=1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

8

Reactant 4

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 68133660(E)-4-(2-Chloro-4-biphenylyl)-3-pentene-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 215471524-(2-Chloro-4-biphenylyl)-2-pentanone

Reagents, catalysts & solvents 3

HCID 62601Nickel acetate tetrahydrateCatalystHCID 82791nickel boride (NiB)CatalystHCID 702EthanolSolvent

Procedure

17.3 Gm (0.0695 mol) of nickel(II)acetate tetrahydrate, dissolved in 600 ml of 95% ethanol, were reduced in a hydrogenation apparatus in a hydrogen atmosphere with 70 ml of a 1 M sodium borohydride solution to black, colloidal nickel boride (P-2-catalyst). To remove any unreacted borohydride which may be present, 16 gm (0.276 mol) of acetone were first added, and then the mixture was shaken at room temperature for 1 hour and, after addition of 35.0 gm (0.129 mol) of (E)-4-(2-chloro-4-biphenylyl)-3-pentene-2-one, hydrogenated at a hydrogen pressure of 5 atmospheres until hydrogen absorption had ceased. The catalyst was filtered off, the filtrate was evaporated in vacuo, and the residue was distributed between the water and ethyl acetate. The organic layer was dried over sodium sulfate and evaporated, and the residue was distilled in a high vacuum. 28.0 Gm (80% of theory) of colorless crystals were obtained which, after recrystallization from methanol, melted 54°-55°C.

Workup

  1. customTo remove any unreacted borohydride which
  2. customhydrogenated at a hydrogen pressure of 5 atmospheres until hydrogen absorption
  3. filtrationThe catalyst was filtered off
  4. customthe filtrate was evaporated in vacuo
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customevaporated
  7. distillationthe residue was distilled in a high vacuum
  8. custom28.0 Gm (80% of theory) of colorless crystals were obtained which
  9. customafter recrystallization from methanol
  10. custommelted 54°-55°C.

Sources & evidence

ORD record
ord-c850b316ba484e319239b134100277ba
Source dataset
uspto-grants-1976_04
Patent number
US03950427

Reaction notes

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