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The Pechmann condensation is a synthesis of coumarins, starting from a phenol and a carboxylic acid or ester containing a β-carbonyl group. The condensation is performed under acidic conditions. The mechanism involves an esterification/transesterification followed by attack of the activated carbonyl ortho to the oxygen to generate the new ring. The final step is a dehydration, as seen following an aldol condensation. It was discovered by the German chemist Hans von Pechmann.
Additional recommended knowledge
With simple phenols, the conditions are harsh, although yields may still be good.
For coumarins unsubstituted at the 4-position, the method requires the use of formylacetic acid or ester. These are unstable and not commercially available, but the acid may be produced in situ from malic acid and sulfuric acid above 100°C. As soon as it forms, the formylacetic acid performs the Pechmann condensation. In the example shown, umbelliferone itself is produced, albeit in low yield:
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Pechmann_condensation". A list of authors is available in Wikipedia.|