First authentication of Kostanecki's triketone and multimolecular reaction of aromatic aldehydes with acetophenone

Abstract

A double-component, multimolecular reaction between acetophenone and aromatic aldehydes was achieved under catalysis by the solid-base mixture NaOH/K2CO3, and Kostanecki's triketone, supposed to exist for more than 110 years, was successfully separated for the first time as an accompaniment of a pentane-1,5-dione or a 1,2,3,4,5-pentasubstituted cyclohexanol (Scheme 1) and authenticated by spectroscopic and single-crystal X-ray diffraction analysis. Thus, the multimolecular-reaction mechanism of the formation of 1,2,3,4,5-pentasubstituted cyclohexanols from 1-phenylalkan-1-ones and aromatic aldehydes was fully validated based on the results (Scheme 3). © 2009 Verlag Helvetica Chimica Acta AG.