Acetic Acid → 4-Chloro-1-naphthol

HRID 262537Notes

Reaction equation

HRID 262537 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12]C)=[CH:4][CH:3]=1.C(O)(=O)C.Br>O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 6060381-Chloro-4-methoxynaphthalene

Product 1

HCID 117874-Chloro-1-naphthol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The known compound 1-chloro-4-methoxynaphthalene is dissolved in 150 ml. of acetic acid and 150 ml. of 48 percent hydrobromic acid, and the mixture is heated at its reflux temperature for two hours. The mixture is diluted with 200 ml. of water and cooled to provide 1-chloro-4-hydroxynaphthalene as a crystalline solid.

Workup

  1. temperaturereflux temperature for two hours
  2. additionThe mixture is diluted with 200 ml

Sources & evidence

ORD record
ord-4d56f003d2c74f3aaaf1273fc672b7bd
Source dataset
uspto-grants-1979_05
Patent number
US04154848

Reaction notes

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