p-METHYLACETOPHENONE → p,alpha-DIMETHYLBENZYL ALCOHOL

Participants

Reaction Conditions

Reaction Steps

Tris(triphenylphosphine)ruthenium(II) chloride (3.8 mg, 4 μmol, 0.5 mol %) and a chiral ligand (M=Ru, R=t-Bu, Ar=C6H5—, 2.6 μmol, 0.33 mol %) were dissolved in ether (3 mL) under nitrogen atmosphere, and then heated and stirred for 1 h at 40° C. After the mixture was cooled to room temperature, p-methylacetophenone (0.8 mmol), ether (2 mL) and a solution of potassium ethoxide in i-propanol (0.4 mL, 0.2 M) were added thereto. Thereafter, the reaction system was placed in an autoclave, and stirred for 12 h under H2 (10 atm) at 25° 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-(p-methylphenyl)ethanol was obtained and the ee value (ee=99.3%) was measured by GC analysis.

Provenance & Evidence