Synthesis of 2,3-dihydrobenzo[1,4]dioxin-6-ol and Its Antioxidant Activity in Oils
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Abstract:
In this paper, the synthesis and antioxidant activity of 2,3-dihydrobenzo[1,4]dioxin-6-ol, a sesamol analogue, are described. Using catechol and 1,2-dichloroethane as starting materials, 1,4-benzodioxane was prepared by cyclization under refluxing basic conditions, and then, Friedel-Crafts acylation was carried out to yield 6-acetyl-1,4-benzodioxane. The final product was obtained after Baeyer-Villiger oxidation, hydrolytic acidification, and column chromatography. The concentration of NaOH solution in the cyclization, the solvent used in the acylation, and the oxidizing agent in the oxidation were optimized. The optimum conditions for each step were as follows: concentration of NaOH, 50%; solvent for the acylation reaction, nitrobenzene; oxidizing agent in the Baeyer-Villiger oxidation, 3-chloroperbenzoic acid. Structural identification and characterization were conducted using infrared spectroscopy, mass spectrometry, and nuclear magnetic resonance spectroscopy (13C-NMR), and the final product was identified as 2,3-dihydro-benzo[1,4]dioxin-6-ol. The antioxidant activity of the obtained product in oils was evaluated, and the results showed that this sesamol analogue displayed antioxidant activity in both animal and vegetable oils.
