Hydrochloric Acid → Benzenediazonium chloride

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In a method for preparing the compound: ##STR3## wherein aniline is diazotized in aqueous hydrochloric acid employing sodium nitrite as the diazotizing agent to form benzenediazonium chloride, the benzenediazonium chloride is coupled into aniline to form aminoazobenzene, and the aminoazobenzene is diazotized and coupled into phenol; the improvement comprising: diazotizing the aniline employing an excess of sodium nitrite of up to about 10% of the amount stoichiometrically required to diazotize one-half of the aniline on a molar basis; coupling the resultant benzenediazonium chloride with the remaining aniline to form a mixture of aminoazobenzene and excess benzenediazonium chloride in aqueous hydrochloric acid; heating said mixture to about 40° C. and allowing said excess benzenediazonium chloride to decompose and, subsequently, without isolation, diazotizing said aminoazobenzene and coupling it into phenol.

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