Acetone → 4-(3-Chloro-4-cyclohexyl-phenyl)-2-butanone

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Reaction Steps

In a hydrogenation apparatus 15 gm (0.06 mol) of nickel(II)acetate tetrahydrate, dissolved in 600 ml of 95% ethanol, were reduced in an atmosphere of hydrogen with 60 ml of a 1 M sodium borohydride solution, to yield black colloidal nickel boride (P-2-catalyst). In order to remove any unreacted borohydride, 14 gm (0.24 mol) of acetone were added, and the resulting mixture was shaken for 1 hour at room temperature and, after addition of 32.32 gm (0.123 mol) of (E)-4-(3-chloro-4-cyclohexyl-phenyl)-3-butene-2-one, it was hydrogenated at 5 atmospheres of hydrogen pressure until hydrogen absorption has ceased. The catalyst was filtered off, and the filtrate was concentrated by evaporation in vacuo. The residue shaken with a mixture of water and ethyl acetate, the organic phase was isolated, dried over sodium sulfate and evaporated, and the residue was distilled in vacuo. 19.0 Gm (58% of theory) of a colorless, viscous oil, b.p. 140°-148°C at 0.03 mm Hg were obtained.

Provenance & Evidence