[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:12]=[CH:13][CH:14]=1)[O:6][CH2:7][C:8](=[O:11])[CH2:9][CH3:10].Cl.[H][H]>CO.C(OCC)(=O)C.CCCCCC>[F:1][C:2]([F:15])([F:16])[C:3]1[CH:4]=[C:5]([CH:12]=[CH:13][CH:14]=1)[O:6][CH2:7][CH:8]([OH:11])[CH2:9][CH3:10]Using a steel capillary, 87.9 g of 1-(3-trifluoromethylphenoxy)butan-2-on, dissolved in 130 ml of methanol and 0.641 g of Ru2Cl4 [(R)-2,2'-bis(diphenylphosphino)-1,1'-dinaphthyl]2 [N(C2 H5)3 ]=Ru2Cl4 [(R)-BINAP]2 [N(C2 H5)3 ] and 1.2 ml of 1N hydrochloric acid are transferred in succession into a steel autoclave under an argon atmosphere. In 3 cycles (20 bar, atmospheric pressure), the argon inert gas is displaced by hydrogen, and the mixture is subsequently hydrogenated at 20° C. under a hydrogen pressure of 80 bar. After 69 hours, the hydrogen uptake has ended. The reaction mixture is removed from the steel autoclave and evaporated on a rotary evaporator. The residue obtained is dissolved in ethyl acetate/n-hexane 1/4 and filtered through a short silica gel column to remove the catalyst. After the collected fractions have been evaporated, the desired product is obtained in a yield of 87.9 g (99% of theory); refractive index nD22 1.4611; [α]36520 -18.7+0.2° (c=1.0 in methanol).
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