From Aromatic Acids and Other Reactants

Phenyl benzoate has been formed in 91% yield by the reaction of a stirred mixture of benzoic acid, phenol, carbon tetrachloride, triethylamine and triphenylphosphine in acetonitrile solution at ambient temperature for 3 hours (ref.6). 

A benzene suspension of phenyl dichlorophosphite added with stirring and cooling to benzoic acid in pyridine during 2 hours gave, after treatment with excess phenol followed by refluxing of the mixture for 4-5 hours, phenyl benzoate in 85% yield (ref.7). 

Diphenyl terephthalate was obtained with a conversion of 99.9% from a mixture of terephthalic acid, phenol, some tetra-n-butyl-1,3-diphenoxydistannoxane and platinum wire (pretreated with hydrogen) heated for 2 hours in an autoclave at 260°C under hydrogen (ref.8). 

Amberlite IRA-400 (chloride form, P CI) converted to the phenoxide form with 0.25M aqueous sodium phenoxide and reacted with a benzene solution of benzoyl chloride afforded phenyl benzoate in 95% yield. The resin was easily recycled by treatment with hydrochloric acid solution (ref.9). 

Aryl halides have been employed for ester formation in two related methods. Thus a mixture of phenol and bromobenzene reacted under a pressure of carbon monoxide (0.1-10.0 Kg/cm2) in the presence of a platinum metal catalyst and a base such as pyridine or triethylamine, afforded phenyl benzoate (ref. 10). 

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