General procedure for the synthesis of 2-(4-(hydroxymethyl)phenyl)acetonitrile from 4-(cyanomethyl)benzoic acid: 1,1'-Carbonyldiimidazole (23.3 g, 0.14 mol) was added batchwise to 600 mL of anhydrous tetrahydrofuran dissolved in 4-(cyanomethyl)benzoic acid (21.2 g, 0.13 mol). The reaction mixture was stirred at room temperature until bubble production was no longer observed. Subsequently, 800 mL of an aqueous solution of sodium borohydride (15 g, 0.39 mol) was slowly added dropwise to the reaction mixture and stirring was continued for 4 hours at room temperature. Upon completion of the reaction, the mixture was extracted with ethyl acetate. The organic layers were combined, washed with saturated saline, dried over anhydrous sodium sulfate, concentrated and purified by rapid chromatography on silica gel to afford the target product 2-(4-(hydroxymethyl)phenyl)acetonitrile as a colorless oil (14.36 g, 74.2% yield). The product characterization data were as follows: 1H NMR (300 MHz, CDCl3) δ 7.37 (d, J = 8.5 Hz, 2H), 7.30 (d, J = 8.5 Hz, 2H), 4.68 (s, 2H), 3.74 (s, 2H); MS (EI): 147 [M]+.
