3,6-dimethoxyxanthone from 2,2’,4,4’- tetrahydroxy-benzophenone via Microwave-Assisted Annulation

Authors

Sarah E. Knisely, Bob Jones UniversityFollow
Faith R. Rosario, Bob Jones UniversityFollow
Salem F. Gebeyehu, Bob Jones UniversityFollow
Paige E. Heiple, Cambrex ChemicalFollow
Robert E. Lee Sr, Bob Jones UniversityFollow

Abstract

Xanthones are tricyclic aromatic compounds that have multiple pharmacological uses due to their anti-tumor, antioxidant, anti-inflammatory, anti-bacterial, and potentially chemopreventive properties. The target of this research was to optimize a two-step synthesis of 3,6-dimethoxyxanthone (3) from 2,2’,4,4’-tetrahydroxy-benzophenone (1) via microwave-assisted (200 °C, 30-40 min., 150 W) sodium acetate-catalyzed annulation. The product, 3,6-dihydroxyxanthone (2), was then methylated to (3) using dimethyl sulfate (DMS) and sodium carbonate in acetone at reflux. The product yields were 93% (>99% purity) for (2) and 94% (>99% purity) for (3). Characterization was accomplished using ¹H NMR, FTIR, melting point, TLC, HPLC, and GCMS. The product (3) was made available for additional screening and research, such as synthesizing dyes like fluorescein and its derivatives.

Recommended Citation

Knisely, Sarah E.; Rosario, Faith R.; Gebeyehu, Salem F.; Heiple, Paige E.; and Lee, Robert E. Sr (2022) "3,6-dimethoxyxanthone from 2,2’,4,4’- tetrahydroxy-benzophenone via Microwave-Assisted Annulation," Journal of the South Carolina Academy of Science: Vol. 20: Iss. 2, Article 6.
Available at: https://scholarcommons.sc.edu/jscas/vol20/iss2/6