The selective oxidation of alcohols to aldehydes traditionally uses toxic reagents and solvents. Previous work from our lab reported a greener synthesis of benzaldehyde from benzyl alcohol using 15% H2O2 in the presence of tetrakis(benzyltriethylammonium) octamolybdate. This preparation was suited for use as a greener organic laboratory experiment.The current work reports the oxidation of alcohols (benzyl and p-methylbenzyl) using greener conditions (3% H2O2) for the preparation of benzaldehyde and p-tolualdehyde.Unexpectedly, attempts to oxidize cinnamyl alcohol to cinnamaldehyde resulted in traces of the desired product along with large amounts of unanticipated products: benzaldehyde and 1-phenyl-1,2-propanedione. Our initial hypothesis for the formation of benzaldehyde from cinnamyl alcohol suggests that cinnamaldehyde may, in fact, form and then undergo a retro-aldol reaction. Results of initial experiments to study that hypothesis will be presented.

Improvement and expansion of the selective oxidation of alcohols: A greener green chemistry laboratory experiment

244th National Meeting (2012)

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