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Auwers synthesis

Lianyungang Klinechem Co.,Ltd | Updated: Nov 29, 2018

The Auwers synthesis is a series of organic reactions forming a flavonol from a coumarone. This reaction was first reported by Karl von Auwers in 1908.[1][2][3][4][5]

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The first step in this procedure is an acid catalyzed aldol condensation between benzaldehyde and a 3-cyclooxapentanone to an o-hydroxychalconeBromination of the alkene group gives a dibromo-adduct which rearranges to the flavonol by reaction with potassium hydroxide.

Mechanism

A possible mechanism for the rearrangement step is shown below:

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References

1.     Jump up^ K. Auwers, K. Müller, "Umwandlung von Benzal-cumaranonen in Flavonole", Ber. Dtsch. Chem. Ges.41, 4233–4241 (1908) (doi:10.1002/cber.190804103137).

2.     Jump up^ K. v. Auwers, P. Pohl, "Über die Umwandlung von Benzalcumaranonen in Flavonole", Liebigs Ann. Chem.405, 243–294 (1914) (doi:10.1002/jlac.19144050302).

3.     Jump up^ K. v. Auwers, P. Pohl, "Eine Synthese des Fisetins", Ber. Dtsch. Chem. Ges.48, 85–90 (1915) (doi:10.1002/cber.19150480114).

4.     Jump up^ K. v. Auwers, "Zur Bildung von Flavonolen aus Benzal-cumaranonen", Ber. Dtsch. Chem. Ges.49, 809–819 (1916) (doi:10.1002/cber.19160490188).

5.     Jump up^ K. v. Auwers, E. Auffenberg, "Über Cumaranone und Hydrindone", Ber. Dtsch. Chem. Ges.52, 92-113 (1919) (doi:10.1002/cber.19190520114).

See also

·         Algar-Flynn-Oyamada reaction

·         Allan-Robinson reaction

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