Benzophenone → HCID 178445811, compound

Participants

Reaction Steps

The effectiveness of ruthenium-aryl-aminophosphine catalysts for the hydrogenation of ketones and aldehydes was investigated. The results are summarized in Tables 1-3. Table 1 shows the hydrogenation of a variety of ketones using complex 1 (FIG. 3) and KOtBu as the catalyst at room temperature. Acetophenone and benzophenone were readily converted to phenylethanol and benzhydrol, respectively. The hydrogenation of 4-tert-butylcyclohexanone was completed at room temperature and resulted in predominantly cis-4-tert-butylcyclohexanol (80%). Cis-4-tert-butylcyclohexanol is very valuable in the fragrance industry since it is used to prepare cis-4-tert-butylcyclohexyl acetate (woody acetate). The hydrogenation of the conjugated ketone benzalacetone resulted in the allyl alcohol as the only detectable product. Likewise, only the carbonyl group of 5-hexen-2-one was reduced to give the unsaturated alcohol. A 95% conversion of the ketone to the alcohol was observed in the reduction of norcamphor resulting in 75% endo-norborneol and 25% exo-norborneol. Benzaldehyde and acetyl ferrocene were converted to the respective alcohols.

Provenance & Evidence