Phenyl benzoate
chemical compound
Phenyl benzoate is an organic compound with the chemical formula C6H5COOC6H5, 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.
Synthesis
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.
C6H5COCl + C6H5OHNaOH→C6H5COOC6H5 + HCl
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.
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