1-(3-Chlorophenyl)ethanone → 3-Chloro-alpha-methylbenzenemethanol

HRID 1855119Notes

Reaction equation

HRID 1855119 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.C[O-].[K+]>C(O)(C)C.[Fe]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 149331-(3-Chlorophenyl)ethanoneHCID 23664618Potassium methoxide

Product 1

HCID 977793-Chloro-alpha-methylbenzenemethanol

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 3776IsopropanolSolvent3×

Conditions

Temperature
85 °C

Procedure

Tris(triphenylphosphine)ruthenium (II) chloride (3.8 mg, 4 μmol, 0.5 mol %) and a chiral ligand (M=Fe, R=t-Bu, Ar=C6H5—, 2.6 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, m-chloroacetophenone (0.8 mmol), i-propanol (2 mL) and a solution of potassium methoxide 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 (50 atm) at 10° C. The solvent was removed under reduced pressure, the resultants were separated by column chromatography (silica gel column; eluent:ethyl acetate/petroleum ether=1/5). Accordingly, pure 1-(m-chlorophenyl)ethanol was obtained and the ee value (ee=98%) was measured by GC analysis.

Workup

  1. temperatureheated
  2. temperatureAfter the mixture was cooled to room temperature
  3. stirringstirred for 24 h under H2 (50 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=1/5)

Sources & evidence

ORD record
ord-0a13bf008b8f4ce5a059faeec063bba4
Source dataset
uspto-grants-2015_02
Patent number
US08962852B2

Reaction notes

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