Synthesis of 5: 6-Dihydroxyflavone and the Structure of Primetin

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Scientific paper

PRIMETIN, C15H10O4, isolated from the leaves of Primula modesta1, has hitherto been regarded as 5: 6-dihydroxyflavone (1), and several attempts have been made to prepare this compound2. An unambiguous synthesis of 5: 6-dimethoxyflavone has now been carried out via the stages 2: 6-dihydroxyacetophenone, 2 -hydroxy-6-methoxyacetophenone, 2: 5-dihydroxy-6-methoxyacetophenone, 2-hydroxy-5: 6-dimethoxyacetophenone, 2-benzoyloxy-5: 6-di-methoxyacetophenone, and 2-hydroxy-5: 6-dimethoxydibenzoylmethane.

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