Auwers synthesis | |
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Named after | Karl von Auwers |
Reaction type | Coupling reaction |
Identifiers | |
RSC ontology ID | RXNO:0000474 |
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]
The first step in this procedure is an acid catalyzed aldol condensation between benzaldehyde and a 3-cyclooxapentanone to an o-hydroxychalcone. Bromination of the alkene group gives a dibromo-adduct which rearranges to the flavonol by reaction with potassium hydroxide.
A possible mechanism for the rearrangement step is shown below:
Auwers synthesis | |
---|---|
Named after | Karl von Auwers |
Reaction type | Coupling reaction |
Identifiers | |
RSC ontology ID | RXNO:0000474 |
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]
The first step in this procedure is an acid catalyzed aldol condensation between benzaldehyde and a 3-cyclooxapentanone to an o-hydroxychalcone. Bromination of the alkene group gives a dibromo-adduct which rearranges to the flavonol by reaction with potassium hydroxide.
A possible mechanism for the rearrangement step is shown below:
Topics in
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