1-Phenyl-1-propanone → 1-Phenyl-1-propanol

HRID 1855136Notes

Reaction equation

HRID 1855136 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:4])[CH2:2][CH3:3].C(=O)([O-])[O-].[Na+].[Na+]>C(O)(C)C.CC1C=CC(C(C)C)=CC=1.CC1C=CC(C(C)C)=CC=1.Cl[Ru]Cl.Cl[Ru]Cl>[C:5]1([CH:1]([OH:4])[CH2:2][CH3:3])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 71481-Phenyl-1-propanoneHCID 10340Sodium Carbonate

Product 1

HCID 71471-Phenyl-1-propanol

Reagents, catalysts & solvents 2

HCID 10908223Dichloro(p-cymene)ruthenium(II) dimerCatalystHCID 3776IsopropanolSolvent3×

Conditions

Temperature
85 °C

Procedure

Dichloro(p-cymene)ruthenium(II) dimer (1.2 mg, 2 μmol, 0.5 mol %) and a chiral ligand (M=Ru, R=i-Pr, Ar=C6H5—, 2.6 μmol, 0.65 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, propiophenone (0.4 mmol), i-propanol (2 mL) and a solution of sodium carbonate in i-propanol (0.4 mL, 0.2 M) were added thereto. Thereafter, the reaction system was placed in an autoclave, and stirred for 24 h under H2 (5 atm) at 10° C. The solvent was removed under reduced pressure, and the resultants were separated by column chromatography (silica gel column; eluent:ethyl acetate/petroleum ether=1/8). Accordingly, pure 1-phenylpropanol 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 (5 atm) at 10° 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=1/8)

Sources & evidence

ORD record
ord-333997e164ad4b999c7433cff3baa45d
Source dataset
uspto-grants-2015_02
Patent number
US08962852B2

Reaction notes

Loading…