Auwers synthesis

Auwers synthesis

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. [K. v. Auwers "et al." "Ber." 1908, "41", 4233.] [K. v. Auwers "et al." "Ber." 1915, "48", 85.] [K. v. Auwers "et al." "Ber." 1916, "49", 809.] [K. v. Auwers, P. Pohl, "Ann." 1914, "405", 243.]

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

References

ee also

* Algar-Flynn-Oyamada reaction
* Allan-Robinson reaction


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