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14.5.3.2.3 Condensation between Aroylacetones and Phloroglucinol Dihydrate

DOI: 10.1055/sos-SD-114-00342

Jiang, B.; Zhu, C.-F.Science of Synthesis Knowledge Updates, (20203337.

The condensation of phloroglucinol dihydrate (31) and α-oxygenated β-diketones is a significant pathway for the generation of 4-methylflavylium salts, which are key components of genuine wine pigments. For example, the one-pot, acid-mediated reaction between aroylacetones (32) and phloroglucinol 31 in the presence of an excess of aqueous hexafluorophosphoric acid provides 4-methylflavylium salts 33. The 4-methylflavylium salts are useful synthetic intermediates, which react with aromatic aldehydes in ethanol under reflux conditions, to give color-stable tricyclic pyranoflavylium pigments 34 (Scheme 9).[‌29‌]

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