Acetic Acid → 2-Naphthalenol, 6-bromo-1-nitroso-

HRID 1090764Notes

Reaction equation

HRID 1090764 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.C(O)(=O)C.[N:17]([O-])=[O:18].[Na+]>O>[N:17]([C:8]1[C:9]2[C:4](=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[OH:12])=[O:18]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 271446-Bromo-2-naphthalenolHCID 23668193Sodium Nitrite

Product 1

HCID 30951612-Naphthalenol, 6-bromo-1-nitroso-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

76.2 g (0.342 mol) of 6-bromo-β-naphthol were suspended in 385 ml of 90%-strength acetic acid and nitrosated for two hours at 4° C. with 28.5 g (0.413 mol) of sodium nitrite in 230 ml of water, and stirring was then continued for 23 h at room temperature. The suspension was then made up to twice its volume by filling up with water and the product formed was filtered off by suction. After drying, 83.8 g (97.3%) of crude 1-nitroso-6-bromo-β-naphthol whose purity is adequate for the further reaction was obtained.

Workup

  1. customthe product formed
  2. filtrationwas filtered off by suction
  3. customAfter drying
  4. custom83.8 g (97.3%) of crude 1-nitroso-6-bromo-β-naphthol whose purity is adequate for the further reaction
  5. customwas obtained

Sources & evidence

ORD record
ord-beaf8548e4914e7e8e816d27b0cb9b25
Source dataset
uspto-grants-1992_01
Patent number
US05082932

Reaction notes

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