2,5-Dichlorobenzoic acid → 5-Chloro-2-(3-chlorophenoxy)benzoic acid

HRID 1733403Notes

Reaction equation

HRID 1733403 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Cl:12][C:13]1[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=1.[H-].[Na+]>C1(C)C=CC=CC=1>[Cl:11][C:8]1[CH:7]=[C:3]([C:2]([O:19][C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([Cl:12])[CH:14]=2)=[CH:10][CH:9]=1)[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 57842,5-Dichlorobenzoic acidHCID 79333-ChlorophenolHCID 24758Sodium hydride

Product 1

HCID 126029655-Chloro-2-(3-chlorophenoxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2,5-dichlorobenzoic acid (5.0 g) and m-chlorophenol (3.35 g) in dry toluene (100 mls) was added sodium hydride (1.25 g) under dry nitrogen. Cuprous bromide (3.0 g) was then added and the mixture stirred under reflux for 3 hrs. The toluene was then removed by distillation under reduced pressure and the residue acidified with dilute hydrochloric acid and extracted with diethyl ether. The ethereal extracts were then washed with water and dried over magnesium sulphate. The ether was then removed under reduced pressure and the residue was crystallised from n-hexane to give the title compound.

Workup

  1. temperatureunder reflux for 3 hrs
  2. customThe toluene was then removed by distillation under reduced pressure
  3. extractionextracted with diethyl ether
  4. washThe ethereal extracts were then washed with water
  5. dry with materialdried over magnesium sulphate
  6. customThe ether was then removed under reduced pressure
  7. customthe residue was crystallised from n-hexane

Sources & evidence

ORD record
ord-08f3638b880d48d593872186086baed6
Source dataset
uspto-grants-1980_12
Patent number
US04242121

Reaction notes

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