Phenolic synonyms

When heated with concentrated hydrochloric acid the amino group is replaced by the hydroxyl group and the phenolic eurhodols are produced.

With zinc dust in presence of caustic soda it yields the secondary alcohol oxanthranol, C 6 H 4: CO Choh: C 6 H 4, with tin and hydrochloric acid, the phenolic compound anthranol, C5H4: CO.

They may be prepared by the reduction of nitro compounds in alkaline solution (using zinc dust and alkali, or a solution of an alkaline stannite as a reducing agent); by oxidation of hydrazo compounds; or by the coupling of a diazotized amine and any compound of a phenolic or aminic type, provided that there is a free para position in the amine or phenol.

Hantzsch (Ber., 18 99, 3 2, pp. 59 o, 3089) considers that the oxyazo compounds are to be classed as pseudoacids, possessing in the free condition the configuration of quinone hydrazones, their salts, however, being of the normal phenolic type.

Hewitt has also attacked the problem by brominating the oxyazobenzenes, and has shown that when the hydrobromic acid produced in the reaction is allowed to remain in the system, a brombenzene-azo-phenol is formed, whilst if it be removed (by the addition of sodium acetate) bromination takes place in the phenolic nucleus; consequently the presence of the mineral acid gives the azo compound a pseudo-quinonoid character, which it does not possess if the mineral acid be removed from the sphere of the reaction.