A mixture of 3,5-dimethylphenol (5.00 g, 40.93 mmol), (±)-glycidol (2.72 mL, 41.01 mmol), triethylamine (0.29 mL, 2.08 mmol), and ethanol (25 mL) was heated and refluxed for about 7 hours. Upon completion of the reaction, ethanol was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography (eluent: petroleum ether solution of 25% ethyl acetate) to afford the target product 3-(3,5-dimethylphenoxy)-1,2-propanediol as a white solid (6.00 g, 75% yield). The melting point of the product was 47-49°C. 1H NMR (400 MHz, CDCl3) δ 2.28 (s, 6H), 3.68-3.87 (m, 2H), 3.94-4.04 (m, 2H), 4.04-4.12 (m, 1H), 6.55 (s, 2H), 6.62 (s, 1H); IR (film) υ3383,2923,. 2875,1600,1462,1324 cm-1; MS 197 (M + 1).
