Kostanecki-Robinson reaction

What is Kostanecki-Robinson reaction?

The Kostanecki-Robinson reaction is a chemical process first described by Kostanecki and Rozycki in 1901. The reaction involves the formation of coumarins and chromones from alkyl o-hydroxyaryl ketone and aliphatic acid anhydride in the presence of the corresponding aliphatic acid sodium salt.

Kostanecki-Robinson reaction - general reaction scheme - Kostanecki-Robinson acylation - Kostanecki-Robinson synthesis
Kostanecki-Robinson reaction

The reaction proceeds through the O-acylation and aldol condensation. Since this reaction resembles the Robinson annulation, it is commonly referred to as the Kostanecki-Robinson reaction. Depending on the specific reaction conditions and substituents, either coumarin or chromone, or both, can be produced.

The use of acetic anhydride and sodium acetate typically produces chromone derivatives. Interestingly, the presence of the α-pyrone ring on the aromatic ketone has no significant impact on the Kostanecki-Robinson reaction.

There are also specific variations of the reaction such as the Kostanecki-Robinson acetylation, which involves the reaction between alkyl o-hydroxyaryl ketone and acetic anhydride, and the Kostanecki-Robinson phenylacetylation, which uses phenylacetic anhydride.

References

v. Kostanecki, S. and Różycki, A. (1901), Ueber eine Bildungsweise von Chromonderivaten. [On a method of formation of chromone derivatives] Ber. Dtsch. Chem. Ges., 34: 102-109. https://doi.org/10.1002/cber.19010340119

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