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How is methyl orange made?

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Methyl orange is synthesized by reaction of sulfanilic acid, sodium nitrite, and dimethylaniline. First, sulfanilic acid is dissolved in dilute aqueous acid. Sodium nitrite is added to produce a diazonium salt This reaction is called diazotization and it is extremely useful in organic synthesis. The nitrous acid provides NO+ which replaces a hydrogen on the -NH3+ group to produce -NH2NO+ and water; a second water is eliminated to produce the -N2+ group. The diazonium salt is then coupled with dimethylaniline. The coupling takes place in the opposite ("para") position from the -N(CH3)2 group: The sodium acetate makes the solution weakly basic; the acetate ion accepts the hydrogen displaced from the dimethylaniline ring. References and notes • The Merck Index, 8th ed., Merck & Co., Rahway NJ, 1968. The index gives the following reference for details on the synthesis of methyl orange: L. Gattermann, Die Praxis des organischen Chemikers, 40th ed., de Gruyter & Co., Berlin, 1961, pp 260- ... more
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