Phenyl benzoate is an organic compound with the chemical formula , often abbreviated as PhCOOPh, where Ph stands for phenyl. It is a white crystalline solid, with odor of geranium. It is the phenyl ester of benzoic acid. It can be obtained by the formal condensation of phenol with benzoic acid.
Phenyl benzoate can be synthesized in good yield by the reaction between benzoyl chloride and phenol in basic conditions, for example using sodium hydroxide as a catalyst.
It can be sinthesized by the reaction of the same reactants, but using quaternary ammonium salts or tertiary amines as catalysts, using polar organic solvents such as dichloromethane and chlorobenzene. Using nonpolar organic solvents, such as n-hexane, benzene and toluene, causes the reaction rate to become slower overall. The order of catalytic activity for various quaternary ammonium salts as catalysts is benzyltributylammonium bromide > tetrabutylammonium hydrogensulfate > tetrabutylammonium bromide > benzyltriethylammonium chloride. The order of catalytic activity for various tertiary amines as catalysts is alkyldimethylamine > triethylamine > tributylamine > trimethylamine. The order of effectiveness of organic solvents is dichloromethane > n-hexane > chlorobenzene > toluene.
Relative orientation of the benzene rings in phenyl benzoate's molecule varies with phase state and temperature.
Phenyl benzoate is used in cosmetics as a preservative. It is a key reagent in the synthesis of soluble polyimides using dianhydride and diamine derivatives. Some phenyl benzoate derivatives possessing a terminal hydroxyl group shows anticancer behavior.