A practical synthesis of flavones from methyl salicylate

Article abstract of DOI:10.1016/S0040-4020(01)87119-2

A facile synthetic method has been developed for the conversion of methyl salicylate (5) into flavones 1a-i in high yields. Compound 5 on treatment with t-butyldimethylsilyl chloride (6) gave the O-silyl protected ester 7. Condensation of this ester 7 with the lithium anion generated from acetophenones 3a-i yielded the 1.3-diarylpropane-1,3-diones 8a-i, which on treatment with glacial acetic acid containing 0.5% H₂SO₄ for 3 h at 95-100°C provided the desired flavones 1a-i in 83-94% yields.