2,2'-Bipyridine → 4-Phenyl-2-butanol

HRID 1016721Notes

Reaction equation

HRID 1016721 reaction equation
[OH-].[K+].N1C=CC=CC=1C1C=CC=CN=1.[CH:15](=[CH:22][C:23](=[O:25])[CH3:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[H][H]>CC(O)C>[C:16]1([CH2:15][CH2:22][C:23](=[O:25])[CH3:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:16]1([CH2:15][CH2:22][CH:23]([OH:25])[CH3:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 14742,2'-BipyridineHCID 14797Potassium HydroxideHCID 159094-Phenyl-3-Buten-2-oneHCID 178418361HCID 178418361, compound

Product 2

HCID 17355Benzyl acetoneYield 19.8%HCID 613024-Phenyl-2-butanolYield 80.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

RuClCp* (cod) (3.8 mg, 0.01 mmol), KOH (0.04 mmol), 2,2′-bipyridyl (3.1 mg, 0.02 mmol) and benzalacetone (730.95 mg, 5.0 mmol) were dissolved into 10 ml of 2-propanol, and deaerated by argon substitution, after which the total amount of the resulting mixture was transferred into a 100-milliliter metallic autoclave. Hydrogen was then charged to a predetermined pressure (50 atm), and the reaction was started at room temperature (28° C.). After the reaction solution was stirred for 3 hours, the reaction pressure was brought back to atmospheric pressure, and the reaction products, 4-phenyl-2-butanone (yield 19.8%) and 4-phenyl-2-butanol (yield 80.2%), were identified and determined by TLC monitor (silica gel: n-hexane/ethyl acetate=4/1) and gas chromatography of the reaction solution.

Workup

  1. customwas started at room temperature
  2. custom(28° C.)
  3. customthe reaction pressure

Sources & evidence

ORD record
ord-96eb9993456448d6b096bb556d600ae3
Source dataset
uspto-grants-2002_11
Patent number
US06476278B1

Reaction notes

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