Solubilities of 2-benzoyl-3-chlorobenzoic acid and 1-chloroanthraquinone in organic solvents of ethyl acetate, acetone, 1,4-dioxane, and toluene were determined experimentally in the temperature range from (273.15 to 323.15) K by gravimetric method. The experimental results indicate that the solubility of 2-benzoyl-3-chlorobenzoic acid and 1-chloroanthraquinone in the solvents increased with an increase in temperature. The solubility data of 1-chloroanthraquinone in the different solvents accord with the following order toluene > ethyl acetate > 1,4-dioxane > acetone, whereas for 2-benzoyl-3-chlorobenzoic acid the order is toluene > 1,4-dioxane > ethyl acetate > acetone. The experimental data were correlated with the modified Apelblat equation, lambda h equation, Wilson model, and NRTL model. The correlation results with the modified Apelblat equation, the lambda h equation, and NRTL model are better than those with the Wilson model. The enthalpy, entropy, and the change of Gibbs free energy of 2-benzoyl-3-chlorobenzoic acid and 1-chloroanthraquinone in the selected organic solvents were calculated from the measured solubility data by using the modified van't Hoff equation. The experimental data and model parameters would be useful for optimizing the preparation and purification process of 1-chloroanthraquinone and 2-benzoyl-3-chlorobenzoic acid in industry.