General procedure for the synthesis of 3-(hydroxymethyl)benzaldehyde from m-toluenedicarboxaldehyde: NaBH4 (1.7 g) was slowly added to a mixed solution of ethanol (100 mL) and tetrahydrofuran (150 mL) of m-toluenedicarboxaldehyde (1b, 20.0 g). The reaction mixture was stirred under ice bath conditions for 6 hours. Upon completion of the reaction, the pH was adjusted to 5-6 with 2 M hydrochloric acid solution to quench the reaction. Subsequently, the solvent was removed by rotary evaporator and the residue was extracted by adding water and ethyl acetate to the residue. The organic phase was washed with saturated NaCl solution and dried with anhydrous Na2SO4 for 8 hours. Finally, the product was purified by silica gel column chromatography using petroleum ether-ethyl acetate (5:1, v/v) as eluent to afford the target compound 3-(hydroxymethyl)benzaldehyde (2b, 16.4 g, 80.2% yield).
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