(E)-4-(2-chloro-4-biphenylyl)-3-pentene-2-ol → HCID 21547088, compound

HRID 1605659Notes

Reaction equation

HRID 1605659 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](/[C:8](/[CH3:13])=[CH:9]/[CH:10]([OH:12])[CH3:11])[CH:5]=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:13])[CH2:9][CH:10]([OH:12])[CH3:11])[CH:5]=[CH:4][C:3]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 1

HCID 21547087(E)-4-(2-chloro-4-biphenylyl)-3-pentene-2-ol

Product 1

HCID 21547088HCID 21547088, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

40.0 Gm (0.147 mol) of (E)-4-(2-chloro-4-biphenylyl)-3-pentene-2-ol, dissolved in 800 ml of ethyl acetate, were hydrogenated at room temperature and at a hydrogen pressure of 3 atmospheres in the presence of 15.0 gm of Raney-nickel until hydrogen absorption had ceased. The catalyst was then filtered off, and the filtrate was evaporated in vacuo. The residue, a colorless, non-crystallizing, highly viscous oil, was purified by chromatography on silicagel, first using benzene and then benzene/ethyl acetate (ratio by volume = 9:1) as the eluant. The product, a mixture of both possible diastereomers, was not stable enough for distillation in a high vacuum. The characterization was effected by IR-, UV- and H-NMR-spectra as well as by elemental analysis:

Workup

  1. customwere hydrogenated at room temperature and at a hydrogen pressure of 3 atmospheres in the presence of 15.0 gm of Raney-nickel until hydrogen absorption
  2. filtrationThe catalyst was then filtered off
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue, a colorless, non-crystallizing, highly viscous oil, was purified by chromatography on silicagel, first using benzene
  5. additionThe product, a mixture of both possible diastereomers
  6. distillationwas not stable enough for distillation in a high vacuum

Sources & evidence

ORD record
ord-82bdbb4b460340a9a4522e0947d25087
Source dataset
uspto-grants-1976_04
Patent number
US03950427

Reaction notes

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