Example 1 Preparation of 2-(2,4,6-trichlorophenoxy)ethanol: In a 1-liter three-necked round-bottomed flask equipped with a stirrer, a thermometer, a reflux condenser, and a gas distributor, 70 g of 2-phenoxyethanol was dissolved in 125 mL of 32% HCl was added (Step I (a)). The reaction mixture was cooled with stirring to 0-25°C and the temperature was maintained at 0°C by passing chlorine at an appropriate rate. cooled to 5°C if necessary. a second liquid phase appeared during the reaction. When about two-thirds of the chlorine has been added (about 7 hours), raise the temperature to 25°C and continue to pass chlorine at a slower rate until the total chlorine addition reaches 125 g (additional 8 hours). Stirring was stopped and the lower organic phase was poured into 100 mL of sodium bisulfite solution at 20° C. The temperature was maintained at 70° C. The pH was adjusted to 7.5 by adding 10% sodium hydroxide solution, stirring was stopped and the lower organic phase was separated. The organic phase was dissolved in 150 mL of methanol and 50 mL of water was added, maintaining the temperature at 45°C. The resulting solution was cooled to 0-5°C to crystallize the product. The crystals were filtered, washed with water and dried to give 2-(2,4,6-trichlorophenoxy)ethanol in 88% yield and 98-99% purity.
