General procedure for the synthesis of p-ethoxybenzyl alcohol from 4-ethoxybenzaldehyde: NaBH4 (0.8 g, 21.7 mmol) was added in batches to a stirring solution of 4-ethoxybenzaldehyde (3.0 g, 19.7 mmol) in methanol (50 mL) at 0 °C, and the addition process lasted for 15 minutes. After the addition, the reaction mixture was continued to be stirred at room temperature for 30 min. After completion of the reaction, the solvent was removed by rotary evaporator to obtain the crude product. The crude product was dissolved in water and extracted twice with ethyl acetate (EtOAc). The organic phases were combined, washed sequentially with water and saturated saline, and dried over anhydrous sodium sulfate. The dried organic phase was concentrated under reduced pressure to give a white solid product, p-ethoxybenzyl alcohol, in 82% yield. The product was analyzed by LC-MS showing [M+H]+ peak of 135.2. 1H-NMR (400 MHz, CDCl3) δ 7.266-7.286 (d, 2H, J = 8.0 Hz), 6.872-6.893 (d, 2H, J = 8.4 Hz), 4.609 (s, 2H), 4.010-4.061 (q, 2H, J = 6.8 Hz), 1.396-1.430 (t, 3H, J = 6.8 Hz).
