3-Hydroxy-2-naphthoic_acid

3-Hydroxy-2-naphthoic acid

3-Hydroxy-2-naphthoic acid

Chemical compound

3-Hydroxy-2-naphthoic acid is an organic compound with the formula C10H6(OH)(CO2H). It is one of the several hydroxynaphthoic acids. It is a precursor to some azo dyes and pigments. It is prepared by carboxylation of 2-naphthol by the Kolbe–Schmitt reaction.[1]

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Reactions

Lithol Rubine BK is one of many dyes made from 3-hydroxy-2-naphthoic acid. Notice that the coupling occurs adjacent to the hydroxy group.

3-Hydroxy-2-naphthoic acid is a precursor to many anilides, such as Naphthol AS, which are reactive toward diazonium salts to give deeply colored azo compounds. Azo coupling of 3-hydroxy-2-naphthoic acid gives many dyes as well. Heating 3-hydroxy-2-naphthoic acid in ammonia give 3-amino-2-naphthoic acid.[2]

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References

  1. [1]
    Gerald Booth (2005). "Naphthalene Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_009. ISBN 9783527303854.
  2. [2]
    Allen, C. F. H.; Bell, Alan (1942). "3-Amino-2-Naphthoic Acid". Organic Syntheses. 22: 19. doi:10.15227/orgsyn.022.0019.
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