GENERAL PROCEDURE: A 1N HCl solution (82.5 mL) was added to a round-bottomed flask containing 6-amino-m-cresol (~1 mmol). Acrolein diethyl acetal (2.5 mmol) was then added. The reaction mixture was refluxed at 111 °C for 24 hours. After completion of the reaction, it was cooled to room temperature and neutralized to pH 7-8 with solid Na2CO3. The product was extracted with dichloromethane (3 x 100 mL), the organic layers were combined, dried with anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography with the eluent being a mixed solvent of hexane/ethyl acetate or 15% ethyl acetate/cyclohexane with methanol to give the target compound 6-methylquinolin-8-ol.
