Hydrogen Bromide → 4-(4-Chlorophenoxy)phenol

HRID 1614111Notes

Reaction equation

HRID 1614111 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([O:13]C)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.Br.C(OCC)C>C(O)(=O)C>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 101054561-Chloro-4-(4-methoxyphenoxy)benzene

Product 1

HCID 123461204-(4-Chlorophenoxy)phenol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The 4-(4'-chlorophenoxy)anisol was demethylated by refluxing it with an excess of 48% HBr in glacial acetic acid for 24 hours. The crude product, obtained after hydrolysis and extraction with diethyl ether, was recrystallized from hexane to yield 4-(4'-chlorophenoxy)phenol as a white solid, bp 83°-85° C., 24.5 g (91.4%).

Workup

  1. customThe crude product, obtained
  2. customwas recrystallized from hexane

Sources & evidence

ORD record
ord-cfb74ed407ea4b96af2017d8eb1a94ef
Source dataset
uspto-grants-1993_03
Patent number
US05196130

Reaction notes

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