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- Title
3,6-dimethoxyxanthone from 2,2',4,4'-tetrahydroxy-benzophenone via Microwave-Assisted Annulation.
- Authors
Knisely, Sarah E.; Rosario, Faith R.; Heiple, Paige E.; Gebeyehu, Salem F.; Lee Sr., Robert E.
- Abstract
Xanthones are tricyclic aromatic compounds that have multiple pharmacological uses due to their anti-tumor, antioxidant, antiinflammatory, 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.
- Subjects
HYDROXYBENZOPHENONES; ANNULATION; DIMETHYL sulfate; FLUORESCEIN; MELTING points; AROMATIC compounds; SODIUM carbonate
- Publication
Journal of the South Carolina Academy of Science, 2022, Vol 20, Issue 2, p13
- ISSN
1553-5975
- Publication type
Article