Reference no: EM13235712

A suspension of vanillin (2.5838 g, 16.98 mmol) and sodium hydroxide (0.022 g, 22 mL, 1M) was coolied in an ice-water bath before adding sodium borohydride (0.41s g, 10.89 mmol) while swirling the mixture. After addition of the sodium borohydride the mixture was removed form the ice-water bath and allowed to mix at room temperature for thirty minutes. After mixing for thirty minutes the mixture was placed in an ice bath and HCL (10 mL, 3M) was added in small portion until the solution was weakly acidic. The reaction was then warmed to room temperature while mixing until crystal formation was complete at which time the reaction mixture was placed into an ice bath for ten minutes. The solid was collected via vacuum filtration, air dried, and recrystalized from hot ethyl acetate. The solid was filtered to yield product (2.618 g, 16.982 mmol, 75.1% yield) as a white crystalline solid: mp 111.7-114.9 °C (lit mp 110-117 °C).