Sodium borohydride (15.6 g, 0.41 mol, 0.57 eq.) was added batchwise to a stirred solution of 4-(2-(azepan-1-yl)ethoxy)benzaldehyde (200 g, 0.72 mol, 1.0 eq.) in methanol (400 mL) at 0 to 5 °C. The reaction mixture was continued to be stirred at this temperature for 30 minutes. The progress of the reaction was monitored by thin layer chromatography (TLC) with the unfolding agent ratio of ethyl acetate/hexane/triethylamine (3:7:1) to confirm that the raw material was completely converted to the product. Upon completion of the reaction, the mixture was diluted with water (400 mL) and extracted with dichloromethane (3 x 400 mL). The organic phases were combined and dried with anhydrous magnesium sulfate. Subsequently, the organic phase was concentrated on a rotary evaporator to afford 201 g (100% yield) of (4-(2-(azepan-1-yl)ethoxy)phenyl)methanol, the product was in the form of a thick oil. The structure of the product was confirmed by 1H NMR (CDCl3/TMS) with the following characteristic peaks: 7.27 (d, 2H, J=8.5Hz), 6.87 (d, 2H, J=8.5Hz), 4.60 (s, 2H), 4.05 (t, 2H, J=6.21Hz), 2.93 (t, 2H, J=6.15Hz), 2.77 (m, 4H ), 1.7-1.5 (m, 8H).
![4-[2-(azepan-1-yl)ethoxy]benzaldehyde](/CAS/GIF/223251-09-0.gif)
