Acetic Acid → 1-Nitro-2-naphthol

HRID 1731061Notes

Reaction equation

HRID 1731061 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. customreaches 45° C
  2. filtrationThe precipitated solids are filtered
  3. washwashed with water
  4. custompurified by chromatography on alumina

Sources & evidence

ORD record
ord-47f0026c24df48838a6f93281f960101
Source dataset
uspto-grants-1976_11
Patent number
US03994968

Reaction notes

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