4-Acetylbiphenyl → 1-([Biphenyl]-4-yl)ethanol

HRID 1855131Notes

Reaction equation

HRID 1855131 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)(C)C>[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([OH:15])[CH3:14])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 71134-AcetylbiphenylHCID 11430Potassium Carbonate

Product 1

HCID 961761-([Biphenyl]-4-yl)ethanol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent3×

Conditions

Temperature
85 °C

Procedure

Tris(triphenylphosphine)ruthenium (II) chloride (1.9 mg, 2 μmol, 0.5 mol %) and a chiral ligand (M=Ru, R=i-Pr, Ar=C6H5—, 1.3 μmol, 0.33 mol %) were dissolved in i-propanol (3 mL) under nitrogen atmosphere, and then heated and stirred for 1 h at 85° C. After the mixture was cooled to room temperature, p-phenyl-acetophenone (0.8 mmol), i-propanol (2 mL) and a solution of potassium carbonate in i-propanol (0.8 mL, 0.2 M) were added thereto. Thereafter, the reaction system was placed in an autoclave, and stirred for 24 h under H2 (10 atm) at −20° C. The solvent was removed under reduced pressure, and the resultants were separated by column chromatography (silica gel column; eluent: ethyl acetate/petroleum ether=1/5). Accordingly, pure 1-(p-phenylphenyl)ethanol was obtained and the ee value (ee=99.2%) was measured by GC analysis.

Workup

  1. temperatureheated
  2. temperatureAfter the mixture was cooled to room temperature
  3. stirringstirred for 24 h under H2 (10 atm) at −20° C
  4. customThe solvent was removed under reduced pressure
  5. customthe resultants were separated by column chromatography (silica gel column; eluent: ethyl acetate/petroleum ether=1/5)

Sources & evidence

ORD record
ord-501781a76bdd4aae95ab7e2e8566cbd4
Source dataset
uspto-grants-2015_02
Patent number
US08962852B2

Reaction notes

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