Surface Modified Nano Fly Ash as an Activator in the Reduction of Ketones

Surface modified nano fly ash has been used as an activator, in the reduction of a few cyclic and acyclic ketones with NaBH4 as reducing agent. Exclusive formation of trans-4--butyl cyclohexanol was observed in such case. Reduction of 3-methylcyclohexanone yielded only cis-3-methylcyclohexanol (equatorial -OH). In case of reduction of other substituted cyclohexanones, propensity to form more of equatorial alcohol was observed. The chemical yields of various alcohols were high (∼95-99%). The rates of reductions of the ketones were also appreciably high. It appears that the silanol groups present in the surface modified fly ash cause nucleophilic activation of the carbonyl groups leading to faster reaction rate. Exclusive formation of the epimer with equatorially disposed -OH group is most likely due to the same reason. Finally, the advantage of the activator lies in its low cost.