4) Synthesis of 3-(4-cyanophenyl)propanol
Borane-tetrahydrofuran complex (1.0 M, 33.0 mL, 33.0 mmol, dissolved in tetrahydrofuran) was slowly added dropwise to a stirred tetrahydrofuran solution (50 mL) of 3-(4-cyanophenyl)propanoic acid (4.40 g, 25.1 mmol). The reaction mixture was stirred continuously for 14 hours at room temperature. Upon completion of the reaction, water (50 mL) and potassium carbonate (10.0 g, 72.4 mmol) were added to the mixture. Subsequently, the mixture was extracted with ethyl acetate, and the combined organic phases were washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to afford 3-(4-cyanophenyl)propanol as a yellow oil (3.20 g, 79% yield).
1H-NMR (200 MHz, CDCl3) δ: 7.58 (2H, d, J = 8.2 Hz), 7.31 (2H, d, J = 8.2 Hz), 3.68 (2H, t, J = 6.2 Hz), 2.79 (2H, t, J = 7.8 Hz), 2.00-1.75 (2H, m).
IR (pure): 3319, 2943, 2229, 1608, 1505, 1415, 1054, 854, 817 cm-1.
