3.3. Synthesis of Mono- (7a, 10a, 12a, 16a) and Di-O-alkyl Derivatives of Naringenin (8a, 11a, 13a, 17a)

To naringenin (7.35 mmol) dissolved in anhydrous acetone (20 mL), anhydrous potassium carbonate (11.02 mmol) and the corresponding alkyl iodide (36.73 mmol) were added. Reactions were performed with stirring at 40–45 °C for 40–96 h. Then, the organic solvent was evaporated, a saturated solution of sodium chloride (40 mL) was added, and extraction with organic solvent (diethyl ether or ethyl acetate) (3 × 50 mL) was carried out. The collected organic fractions were combined, dried over sodium sulfate, evaporated, and the mixture of crude products was separated by column chromatography.