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Kang, H. Von Pechmann Reaction. Encyclopedia. Available online: https://encyclopedia.pub/entry/60872 (accessed on 23 October 2026).
Kang H. Von Pechmann Reaction. Encyclopedia. Available at: https://encyclopedia.pub/entry/60872. Accessed October 23, 2026.
Kang, Helena. "Von Pechmann Reaction" Encyclopedia, https://encyclopedia.pub/entry/60872 (accessed October 23, 2026).
Kang, H. (2026, October 12). Von Pechmann Reaction. In Encyclopedia. https://encyclopedia.pub/entry/60872
Kang, Helena. "Von Pechmann Reaction." Encyclopedia. Web. 12 October, 2026.

Von Pechmann Reaction

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The von Pechmann reaction, commonly called the Pechmann condensation, forms a coumarin by acid-catalyzed condensation of a phenol with a β-ketoester or β-keto acid derivative. Acid activation enables transesterification or direct electrophilic acylation of the phenolic oxygen, followed by intramolecular electrophilic aromatic substitution at an ortho position, dehydration, and formation of the fused α-pyrone ring [1]. The β-keto component supplies the carbonyl-containing three-carbon unit, while the phenol supplies the benzene ring and ring oxygen of the coumarin. Substituent placement follows the orientation of the phenolic ring and the constitution of the β-keto reagent [2]. The transformation is distinct from the Perkin and Knoevenagel routes to coumarins because it constructs the heterocycle directly from a phenol and a β-carbonyl carboxylic derivative under acidic conditions. Formation of the fused 2H-chromen-2-one framework is its defining structural outcome.

von Pechmann reaction Pechmann condensation coumarin β-ketoester
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References

  1. Melita Lončarić; Dajana Gašo-Sokač; Stela Jokić; Maja Molnar; Recent Advances in the Synthesis of Coumarin Derivatives from Different Starting Materials. Biomol. 2020, 10, 151. [CrossRef]
  2. Andrea Citarella; Serena Vittorio; Christian Dank; Laura Ielo; Syntheses, reactivity, and biological applications of coumarins. Front. Chem. 2024, 12, 1362992. [CrossRef]
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Subjects: Chemistry, Organic
Contributor MDPI registered users' name will be linked to their SciProfiles pages. To register with us, please refer to https://encyclopedia.pub/register : Helena Kang
View Times: 2
Entry Collection: Organic Chemistry
Revision: 1 time (View History)
Update Date: 19 Oct 2026
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