New observation on a class of old reactions: Chemoselectivity for the solvent-free reaction of aromatic aldehydes with alkylketones catalyzed by a double-component inorganic base system

Solvent-free reactions of aromatic aldehydes with three representative ketones, including acetophenone, acetone and cyclohexanone, have been examined under the catalysis of a low-cost inorganic base system consisting of NaOH and K₂CO₃. It was found that the chemoselectivity of the reactions is in close relationship with the composition of the reactants and the doublecomponent catalyst. Under the optimized experimental conditions, 1,2,3,4,5-pentasubstituted cyclohexanols, α,β-unsaturated ketones and Claisen-Schmidt bicondensation products were obtained in high yields. Two Kostanecki’s triketones were separated, The composition and structure were affirmed by X-ray crystallographic analysis.