1,6-Naphthalenediol → 6-hydroxy-1,4-naphthoquinone

HRID 2300576Notes

Reaction equation

HRID 2300576 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:12])=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.N(S([O-])(=O)=O)(S([O-])(=O)=[O:16])[O].[K+].[K+]>CO.OP([O-])(O)=O.[K+].O>[OH:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[C:2](=[O:1])[CH:3]=[CH:4][C:5]2=[O:16]

Participants

6

Reactant 2

HCID 684631,6-NaphthalenediolHCID 3032624Potassium nitrosodisulfonate

Product 1

HCID 118195036-hydroxy-1,4-naphthoquinone

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 516951Monobasic potassium phosphateSolvent

Procedure

1,6-Dihydroxynaphtalene from Aldrich (3.0 g, 18.7 mmol) was dissolved in a mixture of MeOH (150 mL), KH2PO4-solution (0.167 M, 150 mL) and water (200 mL), and Potassium nitrosodisulfonate (Fremy's salt) (12.0 g, 44.7 mmol) was added. The mixture was stirred at room temperature 2 h. The reaction mixture was put in refrigerator and then filtered. Yield 3.0 g. 1H NMR (400 MHz, CD3OD) δ 6.90 (d, 2 H), 7.12 (dd, 1 H), 7.34 (d, 1 H), 7.92 (d, 1 H).

Workup

  1. additionwas added
  2. filtrationfiltered

Sources & evidence

ORD record
ord-5db0af3ed1fb4ad3a0fbe333313408f8
Source dataset
uspto-grants-2002_12
Patent number
US06498182B2

Reaction notes

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