Acetone → 4-(3-Chloro-4-cyclohexyl-phenyl)-2-butanone

HRID 1605671Notes

Reaction equation

HRID 1605671 reaction equation
[BH4-].CC(C)=O.[Cl:6][C:7]1[CH:8]=[C:9](/[CH:19]=[CH:20]/[C:21](=[O:23])[CH3:22])[CH:10]=[CH:11][C:12]=1[CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>>[Cl:6][C:7]1[CH:8]=[C:9]([CH2:19][CH2:20][C:21](=[O:23])[CH3:22])[CH:10]=[CH:11][C:12]=1[CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 3

HCID 180AcetoneHCID 28123BorohydrideHCID 21547138(E)-4-(3-Chloro-4-cyclohexyl-phenyl)-3-butene-2-one

Product 1

HCID 215471084-(3-Chloro-4-cyclohexyl-phenyl)-2-butanone

Procedure

In a hydrogenation apparatus 15 gm (0.06 mol) of nickel(II)acetate tetrahydrate, dissolved in 600 ml of 95% ethanol, were reduced in an atmosphere of hydrogen with 60 ml of a 1 M sodium borohydride solution, to yield black colloidal nickel boride (P-2-catalyst). In order to remove any unreacted borohydride, 14 gm (0.24 mol) of acetone were added, and the resulting mixture was shaken for 1 hour at room temperature and, after addition of 32.32 gm (0.123 mol) of (E)-4-(3-chloro-4-cyclohexyl-phenyl)-3-butene-2-one, it was hydrogenated at 5 atmospheres of hydrogen pressure until hydrogen absorption has ceased. The catalyst was filtered off, and the filtrate was concentrated by evaporation in vacuo. The residue shaken with a mixture of water and ethyl acetate, the organic phase was isolated, dried over sodium sulfate and evaporated, and the residue was distilled in vacuo. 19.0 Gm (58% of theory) of a colorless, viscous oil, b.p. 140°-148°C at 0.03 mm Hg were obtained.

Workup

  1. additionwere added
  2. customwas hydrogenated at 5 atmospheres of hydrogen pressure until hydrogen absorption
  3. filtrationThe catalyst was filtered off
  4. concentrationthe filtrate was concentrated by evaporation in vacuo
  5. stirringThe residue shaken with a mixture of water and ethyl acetate
  6. customthe organic phase was isolated
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. distillationthe residue was distilled in vacuo
  10. custom19.0 Gm (58% of theory) of a colorless, viscous oil, b.p. 140°-148°C at 0.03 mm Hg were obtained

Sources & evidence

ORD record
ord-07ef4a62b68c489c88f0b4baca12056b
Source dataset
uspto-grants-1976_04
Patent number
US03950427

Reaction notes

Loading…