To a mixture of 138.1 g. (1 mole) of salicyclic acid and 128.6 g. (1 mole) of p-chlorophenol in a 2-l. round-bottomed flask fitted with a thermometer reaching to the bottom of the flask and a reflux condenser with a drying tube (Note 1) is added 58.3 g. (0.38 mole) of phosphorus oxychloride. The mixture is heated with occasional swirling, and the temperature is maintained at 75–80°. At the end of 4 hours the reactants have been reduced to a molten mass, and this is poured slowly, with vigorous stirring, into a solution of 120 g. of sodium carbonate in 800 ml. of water. The precipitated ester is collected on a filter and washed with four 200-ml. portions of water. The yield of crude, air-dried, p-chlorophenyl salicylate is 174–189 g. (70–76%); m.p. 65–66°. Recrystallization from absolute ethanol yields 136–154 g. (55–62%) of pure product; m.p. 69.5–70.5°. A second crop may be obtained by concentration of the filtrate from the first crop or by the addition of water (Note 2).