1-Naphthol
chemical compound
1-Naphthol, or α-naphthol, is an organic compound with the formula C10H7OH. It is a fluorescent white solid. 1-Naphthol differs from its isomer 2-naphthol by the location of the hydroxyl group on the naphthalene ring. The naphthols are naphthalene homologues of phenol. Both isomers are soluble in simple organic solvents. They are precursors to a variety of useful compounds.
Production
1-Naphthol is prepared by two main routes. In one method, naphthalene is nitrated to give 1-nitronaphthalene, which is hydrogenated to the amine followed by hydrolysis:
C10H8 + HNO3 → C10H7NO2 + H2O
C10H7NO2 + 3H2 → C10H7NH2 + 2H2O
C10H7NH2 + H2O → C10H7OH + NH3
Alternatively, naphthalene is hydrogenated to tetralin, which is oxidized to 1-tetralone, which undergoes dehydrogenation.
Reactions
Some reactions of 1-naphthol are explicable with reference to its tautomerism, which produces a small amount of the keto tautomer.
One consequence of this tautomerism is the Bucherer reaction: the ammonolysis of 1-naphthol to give 1-aminonaphthalene. Low temperature sulfonation of 1-naphthol gives 1-hydroxynaphthalene-2-sulfonic acid.
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