7-Methoxy-2-naphthol → 7-Methoxy-1-nitrosonaphthalen-2-ol

HRID 1090762Notes

Reaction equation

HRID 1090762 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([OH:13])=[CH:10]2)=[CH:5][CH:4]=1.[N:14]([O-])=[O:15].[Na+]>C(O)(=O)C.O>[N:14]([C:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=2)[CH:7]=[CH:8][C:9]=1[OH:13])=[O:15]

Participants

5

Reactant 2

HCID 8531737-Methoxy-2-naphtholHCID 23668193Sodium Nitrite

Product 1

HCID 28330807-Methoxy-1-nitrosonaphthalen-2-olYield 93.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent3×

Procedure

110.2 g (0.633 mol) of 7-methoxy-β-naphthol were nitrosated in a mixture of 650 ml of glacial acetic acid and 65 ml of water at 0° C. in the course of two hours using a solution of 45.0 g (0.65 mol) of sodium nitrite in 340 ml of water. Stirring was continued for a further two hours and in this time the temperature of the reaction mixture was allowed to rise to 22° C. Then the volume was made up to 1.6 l with water and the precipitated product was filtered off by suction. After drying, 120.3 g (93.5%) of 1-nitroso-7-methoxy-β-naphthol were obtained.

Workup

  1. customto rise to 22° C
  2. filtrationthe precipitated product was filtered off by suction
  3. customAfter drying

Sources & evidence

ORD record
ord-dc7c59247c924b6d8c3e89f5c51363f6
Source dataset
uspto-grants-1992_01
Patent number
US05082932

Reaction notes

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