The goal of this investigation was to improve yields in the synthesis of different flavones by controlling both the amount of time spent on the initial esterification as well as the organic solvents. Flavones are a naturally occurring sub group of flavonoids (found in many plant tissues) which are centered on a 2-phenyl-1-benzopyran-4-one backbone. Flavones have been indicated as having possible applications in medicine including anticancer properties, neurogenesis promotion, antimicrobial and antiviral activities A three step, green synthesis using microscale techniques began with the esterification of 2- hydroxyacetophenone using various benzoyl chlorides, followed by an intramolecular Baker-Venkataraman rearrangement to β-Diketones, and finally an acid catalyzed synthesis producing the flavones. In the esterification reactions of 2-hydroxyacetophenones with the benzoyl chlorides, the amount of time spent on synthesis and recrystallization was varied producing different yields. Results indicate that these methods improve yields and are suitable for an undergraduate organic second semester lab.

Investigations of green and microscale methods in the synthesis of several flavones

249th National Meeting (2015)

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