Potassium Hydroxide → HCID 63410218, compound

Participants

Reaction Conditions

Reaction Steps

Tris(triphenylphosphine)ruthenium (II) chloride (1.9 mg, 2 μmol, 0.5 mol %) and a chiral ligand (M=Ru, R=t-Bu, Ar=C6H5—, 1.3 μmol, 0.33 mol %) were dissolved in xylene (3 mL) under nitrogen atmosphere, and then heated and stirred for 2 h at 140° C. After the mixture was cooled to room temperature, p-methyloctanophenone (0.8 mmol), xylene (2 mL) and a solution of potassium hydroxide in methanol (0.8 mL, 0.2 M) were added thereto. Thereafter, the reaction system was placed in an autoclave, and stirred for 6 h under H2 (10 atm) at 50° 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) octanol was obtained and the ee value (ee=99.0%) was measured by GC analysis.

Provenance & Evidence