2-Chloropyridine (1) (0.002 mol) and p-hydroxybenzaldehyde (2) (0.002 mol) were added with potassium carbonate (0.002 mol) and 10 mL of anhydrous dimethylformamide (DMF) in a round bottom flask, and the reaction was heated for 3-4 hours at 70°C. After completion of the reaction, the mixture was concentrated under reduced pressure, poured into water and extracted with ethyl acetate. The organic phases were combined, washed with water and dried over anhydrous sodium sulfate. Purification by column chromatography (silica gel G, unfolding agent was ethyl acetate:ethanol=3:2) gave the target product 4-(pyridin-2-yloxy)benzaldehyde in 66.8% yield. The product was detected by TLC (Rf 0.65, iodine vapor color development) showed a single spot, melting point 79-81 ℃, molecular weight 199.21.
