Ethanone, 1-(2-chlorophenyl)- → 1-(2-Chlorophenyl)ethanol

HRID 1855120Notes

Reaction equation

HRID 1855120 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].CC(C)([O-])C.[Na+]>CO.C1C=CC=CC=1.C1C=CC=CC=1.Cl[Ru]Cl.Cl[Ru]Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([OH:10])[CH3:9]

Participants

5

Reactant 2

HCID 72864Ethanone, 1-(2-chlorophenyl)-HCID 23676156Sodium t-butoxide

Product 1

HCID 260821-(2-Chlorophenyl)ethanol

Reagents, catalysts & solvents 2

HCID 10962144Benzeneruthenium(II) Chloride DimerCatalystHCID 887MethanolSolvent3×

Conditions

Temperature
65 °C

Procedure

Benzeneruthenium(II) chloride dimer (0.5 mg, 1 μmol, 0.25 mol %) and a chiral ligand (M=Ru, R=t-Bu, Ar=C6H5—, 2.6 μmol, 0.33 mol %) were dissolved in methanol (3 mL) under nitrogen atmosphere, and then heated and stirred for 2 h at 65° C. After the mixture was cooled to room temperature, o-chloroacetophenone (0.8 mmol), methanol (2 mL) and a solution of sodium t-butoxide in methanol (0.4 mL, 0.2 M) were added thereto. Thereafter, the reaction system was placed in an autoclave, and stirred for 6 h under H2 (40 atm) at 50° 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-(o-chlorophenyl)ethanol was obtained and the ee value (ee=97%) was measured by GC analysis.

Workup

  1. temperatureheated
  2. temperatureAfter the mixture was cooled to room temperature
  3. stirringstirred for 6 h under H2 (40 atm) at 50° 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-6c115e74007540ad9e705848eaa7e3b9
Source dataset
uspto-grants-2015_02
Patent number
US08962852B2

Reaction notes

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