Acetic Acid → 1-Nitro-2-naphthol

HRID 1657532Notes

Reaction equation

HRID 1657532 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.C(O)(=O)C.[N+:16]([O-])([OH:18])=[O:17]>O>[N+:16]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]=1[OH:1])([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 86632-Naphthol

Product 1

HCID 110751-Nitro-2-naphthol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-hydroxynaphthalene (1 g.) is dissolved in boiling acetic acid (30 ml.), and when the solution temperature reaches 45'C, a molecular equivalent amount of concentrated nitric acid is slowly added. After standing overnight at room temperature, the reaction mixture is mixed with water. The precipitated solids are filtered, washed with water, and purified by chromatography on alumina, to yield 1-nitro-2-hydroxynaphthalene.

Workup

  1. filtrationThe precipitated solids are filtered
  2. washwashed with water
  3. custompurified by chromatography on alumina

Sources & evidence

ORD record
ord-a21d9562bc6f4e1faf06d6138e023f55
Source dataset
uspto-grants-1976_06
Patent number
US03960957

Reaction notes

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