Acetic Acid → 4-Chloro-1-naphthol

HRID 65727

Reaction equation

HRID 65727 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 2 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 2 hours
  2. additionThe mixture is diluted with 200 ml

Sources & evidence

ORD record
ord-03d39e03caed4569923ddc9bb0d2b986
Source dataset
uspto-grants-1978_12
Patent number
US04128659

Linked notes

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