Benzohydryl benzoate

On standing, diphenyldiazomethane decomposes to yield benzophenone azine. In one of the checkers runs the product was stored at room temperature after 2 days, crystals of the azine were visible. The product at this stage was assayed by treatment with benzoic acid addition of 6.8 g. of the diazo compound in a thin stream to a solution of 17 g. of benzoic acid in 90 ml. of ether, and, after 30 minutes, extraction of the excess benzoic acid with dilute sodium hydroxide followed by distillation of the ether, gave 7.4 g. (75%) of crude benzohydryl benzoate melting at 83-85°. In the same procedure the freshly prepared diazo compound gave a quantitative yield of the crude ester. 

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