Hydrogen Peroxide → Naphthalene

HRID 904751Notes

Reaction equation

HRID 904751 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.F>>[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.[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].[CH:9]1[C:10]2[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 931NaphthaleneHCID 14917Hydrofluoric Acid

Product 3

HCID 931NaphthaleneYield 48%HCID 70051-NaphtholYield 42.3%HCID 86632-NaphtholYield 0.7%

Procedure

When carrying out the hydroxylation of naphthalene with a molar excess of H2O2 (90%) in a conventional acid system, such as anhydrous hydrogen fluoride, at temperatures ranging from -10° to 0° C. and at atmospheric or slightly superatmospheric pressure, 42.3% α-naphthol and only 0.7% β-naphthol were obtained, with about 9% of polymeric higher molecular weight product and 48% of naphthalene can be recovered unchanged. The yield of α-naphthol is 81% with an isomeric purity of 98.4%.

Workup

  1. customranging from -10° to 0° C.

Sources & evidence

ORD record
ord-50bd0ef1628d45e0bfdafea5a3fffe7b
Source dataset
uspto-grants-1983_12
Patent number
US04419528

Reaction notes

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