Acetic Acid → 4-Chloro-1-naphthol

HRID 1154764Notes

Reaction equation

HRID 1154764 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-cf98ec7481b9439296a23a163b3da4a2
Source dataset
uspto-grants-1981_11
Patent number
US04298532

Reaction notes

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