Hydrogen Peroxide → 2-Naphthol

HRID 904754Notes

Reaction equation

HRID 904754 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH:11]O>S(F)(=O)(=O)O>[CH:9]1[C:10]2[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=2)[CH:6]=[CH:7][C:8]=1[OH:11].[C:9]1([OH:11])[C:10]2[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 931Naphthalene

Product 2

HCID 70051-NaphtholYield 3%HCID 86632-NaphtholYield 37%

Reagents, catalysts & solvents 1

HCID 24603Fluorosulfuric acidSolvent2×

Procedure

To a vigorously stirred suspension of 0.1 mol of naphthalene in 100 ml of fluorosulfuric acid at -78° C. was added an equally cold solution of 0.12 mol of H2O2 (90% solution) in 100 ml of fluorosulfuric acid. The reaction mixture was stirred for 30 minutes, then quenched with ice water, and worked up and analyzed as in Example 1. 39% naphthalene was recovered unchanged. 37% of β-naphthol and 3% of α-naphthol were obtained, together with 17% of dihydroxynaphthalenes and 5% polymeric material.

Workup

  1. customquenched with ice water
  2. custom39% naphthalene was recovered unchanged

Sources & evidence

ORD record
ord-5086c3c702c94897bda85cda260f95fc
Source dataset
uspto-grants-1983_12
Patent number
US04419528

Reaction notes

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