A New Approach to the Synthesis of Bergapten

Abstract

In this study, bergapten was synthesized in a yield of 55% from phloroglucinol as starting material, via a novel approach including monomethylation, Hoesch reaction, acetylation, deacetoxylation, Pechmann condensation and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone(DDQ) dehydrogenation. With the adoption of the acetylation of enol tautomer, the deacetoxylation and the DDQ dehydrogenation, the novel approach differs greatly from the processes reported previously, though the starting material was the same or similar to those used on previous synthetic processes. The newly adopted reaction underwent easily, affording all reactions in high yields, especially acetylation and deacetoxylation and DDQ dehydrogenation in almost quantitative yields, ensuring a final yield higher than those previously reported.

Keywords

Bergapten / Enol tautomerism / Acetylation / Deacetoxylation / 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone(DDQ) dehydrogenation

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