Methyl trifluoromethanesulfonate (0.88 mmol) was added to a solution of 2-(3-(pentane-3-yl)phenoxy)pyridine in dry toluene, and the solution was stirred at 100°C for 2 hours under N2 atmosphere. The reaction mixture was cooled to ambient temperature, the solvent was evaporated under vacuum, the crude product was dissolved in dry methanol, and a solution of metallic sodium (12 mmol) in dry methanol was added under N2 atmosphere. The reaction mixture was heated to reflux for 15 minutes, and then cooled to room temperature. After the reaction was complete, the solvent was evaporated under vacuum and water (70 mL) was added. The reaction mixture was extracted with ethyl acetate (50 mL × 3), the combined organic layers were dried on anhydrous Na2SO4, the solution was concentrated under vacuum, and the residue was purified by silica gel column chromatography (PE/EtOAc 6:1 as eluent) to give 3-tert-butylphenol.
Figure 3. Synthetic Route of 3-tert-Butylphenol
