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Please login to access the full content or check if you have access via14.5.3.2.3 Condensation between Aroylacetones and Phloroglucinol Dihydrate
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Jiang, B.; Zhu, C.-F., Science of Synthesis Knowledge Updates, (2020) 3, 337.
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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M8 | Me8 | Meeee (%) | Mee |
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8,8,8-(MeM)8M8M8 | 8-MeMM8M8 | 88 | [88] |
8,8,8-(MeM)8M8M8 | 8-Me8MM8M8 | 88 | [88] |
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References
[29] | Meeeeeeee, M.; Meeeee-Meeeee, M.; Meeee-Meeee, M.; Meeeeeeeee, M., Meeeeeeeeee, (8888) 88, 8888. |