Ethanone, 1-(3,4-dichlorophenyl)- → 3,4-Dichloro-alpha-methylbenzenemethanol
Reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[C:6]([Cl:11])[CH:5]=1)=[O:3].CC(C)([O-])C.[K+]>C(O)(C)C.C1C=CC=CC=1.C1C=CC=CC=1.Cl[Ru]Cl.Cl[Ru]Cl.[Fe]>[Cl:11][C:6]1[CH:5]=[C:4]([CH:2]([OH:3])[CH3:1])[CH:9]=[CH:8][C:7]=1[Cl:10]Participants
Conditions
- Temperature
- 85 °C
Procedure
Benzeneruthenium(II) chloride dimer (1.0 mg, 2 μmol, 0.5 mol %) and a chiral ligand (M=Fe, R=s-Bu, Ar=C6H5—, 2.6 μmol, 0.65 mol %) were dissolved in i-propanol (3 mL) under nitrogen atmosphere, and then heated and stirred for 0.5 h at 85° C. After the mixture was cooled to room temperature, 3,4-dichloroacetophenone (0.4 mmol), i-propanol (3 mL) and a solution of potassium t-butoxide in i-propanol (0.4 mL, 0.2 M) were added thereto. Thereafter, the reaction system was placed in an autoclave, and stirred for 72 h under H2 (3 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-(3,4-dichlorophenyl)ethanol was obtained and the ee value (ee=95%) was measured by GC analysis.
Workup
- temperatureheated
- temperatureAfter the mixture was cooled to room temperature
- stirringstirred for 72 h under H2 (3 atm) at −20° C
- customThe solvent was removed under reduced pressure
- customthe resultants were separated by column chromatography (silica gel column; eluent: ethyl acetate/petroleum ether=1/5)
Sources & evidence
- ORD record
- ord-febf41ed86664d8290a5fbb4482a9cf1
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08962852B2
Reaction notes
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