2-(1-hydroxyethyl)phenol

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Tris(triphenylphosphine)ruthenium (II) chloride (1.9 mg, 2 μmol, 0.5 mol %) and a chiral ligand (M=Ru, R=Ph, Ar=C6H5—, 1.3 μmol, 0.33 mol %) were dissolved in xylene (3 mL) under nitrogen atmosphere, and then heated and stirred for 1 h at 140° C. After the mixture was cooled to room temperature, o-hydroxyacetophenone (0.4 mmol), xylene (2 mL) and an aqueous solution of sodium hydroxide (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=1/2). Accordingly, pure 1-(o-hydroxylphenyl)ethanol was obtained and the ee value (ee=97%) was measured by GC analysis. heated After the mixture was cooled to room temperature stirred for 12 h under H2 (10 atm) at 25° C The solvent was removed under reduced pressure the resultants were separated by column chromatography (silica gel column; eluent:ethyl acetate/petroleum ether=1/2)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 10 g of 2-(2-hydroxyphenyl-ethanol in 200 ml of acetone there are added 35.3 g of Cs2CO3 and then a solution of 6.5 ml of methyl iodide in 40 ml of acetone. The reaction mixture is stirred for 50 minutes at room temperature, is filtered and is concentrated by evaporation. The residue is partitioned between diethyl ether and water. The organic phases are combined, dried over magnesium sulfate and concentrated by evaporation, and the residue is purified by means of FC (dichloromethane/diethyl ether=97:3), yielding the title compound; Rf (dichloromethane/diethyl ether=97:3)=0.34; HPLC Rt =9.31 minutes. is filtered is concentrated by evaporation The residue is partitioned between diethyl ether and water dried over magnesium sulfate concentrated by evaporation the residue is purified by means of FC (dichloromethane/diethyl ether=97:3)