Ethanone, 1-(3,4-dichlorophenyl)- → 3,4-Dichloro-alpha-methylbenzenemethanol

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence