preparation | 4-chloro-3-hydroxybenzaldehyde is prepared as follows: p-toluenesulfonic acid (3.4g,20mmol) is added to acetonitrile (50mL) solution of 3-hydroxybenzaldehyde (1g,10mmol) in batches. The mixture was stirred at room temperature for 5 minutes, NCS(1.33g,10mmol) was added, and the resulting mixture was stirred at room temperature for 2 hours. The mixture was quenched with an aqueous solution of sodium thiosulfate and diluted with ethyl acetate and brine. The organic layer was separated, dried and concentrated to obtain the crude product, which was purified by silica gel chromatography and eluted with petroleum ether/ethyl acetate (10:1 to 5:1) to obtain 4-chloro-3-hydroxybenzaldehyde (310mg,19.7%), which is a yellow solid. |