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Kostanecki acylation

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Kostanecki acylation
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The Kostanecki acylation is a method used in organic synthesis to form chromones[1] or coumarins[2] by acylation of O-hydroxyaryl ketones with aliphatic acid anhydrides, followed by cyclization.[3] If benzoic anhydride (or benzoyl chloride) is used, a particular type of chromone called a flavone is obtained. It was named after Polish chemist Stanisław Kostanecki.

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Mechanism

The mechanism consists of three well-differentiated reactions:[4][5]

  1. Phenol O-acylation with formation of a tetrahedral intermediate
  2. Intramolecular aldol condensation to cyclize and to form a hydroxydihydrochromone
  3. Elimination of the hydroxyl group to form the chromone (or coumarin)
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Examples

See also

References

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