In an improved procedure, chrysin (I) was alkylated with prenyl bromide (II) under phase-transfer conditions, and the resulting prenyl ether (III) was subsequently rearranged under microwave irradiation to produce a mixture of the title compound as the major product along with the 6-prenyl (VI) and the 6,8-diprenyl (VII) derivatives, which were separated by column chromatography.
Alkylation of chrysin (I) with prenyl bromide (II) in the presence of K2CO3 in acetone provided 7-O-(3,3-dimethylallyl)chrysin (III). Claisen rearrangement of (III) in the presence of NaOAc in refluxing Ac2O gave rise to the 8-(1,1-dimethylallyl) flavone (IV) and minor amounts of the desired 8-(3,3-dimethylallyl) analogue (V). Saponification of the mixture of acetate esters, followed by chromatographic separation, furnished the title 8-(3,3-dimethylallyl)chrysin.