P-Chloroacetophenone → Benzenemethanol, 4-chloro-alpha-methyl-

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Tris(triphenylphosphine)ruthenium(II) chloride (3.8 mg, 4 μmol, 1 mol %) and a chiral ligand (M=Fe, R=n-Pr, Ar=C6H5—, 2.6 μmol, 0.65 mol %) were dissolved in ethanol (3 mL) under nitrogen atmosphere, and then heated and stirred for 2 h at 80° C. After the mixture was cooled to room temperature, p-chloroacetophenone (0.4 mmol), ethanol (2 mL) and a solution of sodium ethoxide in ethanol (0.2 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 0° 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-(p-chlorophenyl)ethanol was obtained and the ee value (ee=97%) was measured by GC analysis.

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