Abstract: The preparation of o-hydroxyldiphenyl via diazotization and hydrolysis of o-aminodiphenyl ether involves the competition between hydrolysis and intra-molecular condensation, and there is no report about it so far. A series of effect factors related to the reactions were discussed, especially, the effects of substituents, metals and their ions. The rules of intra-molecular condensation of diazonium salt of o-aminodiphenyl ether under the catalysis of metallic ions were suggested, and the mechanism also was predicted. Metals and their ions may have an obvious catalytic effect on the intra-molecule condensation of o-aminodiphenyl ether diazonium salt, and few effect on hydrolysis. The intra-molecule condensation would be accelerated if there was any metal or its ion in the reaction system, and it led largely to the increase of the product of dibenzofurans.

Key words: o-Aminodiphenyl ether diazonium salt, Hydrolysis reaction, Intra-molecular condensation, Metallic ion catalysis, Mechanism