2,5-Dichlorobenzoic acid → 3-Chloro-6-(3,5-diisopropylphenoxy)benzoic Acid

HRID 1733405

Reaction equation

HRID 1733405 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].[CH:12]([C:15]1[CH:16]=[C:17]([OH:24])[CH:18]=[C:19]([CH:21]([CH3:23])[CH3:22])[CH:20]=1)([CH3:14])[CH3:13].[H-].[Na+]>C1(C)C(C)=CC=CC=1>[Cl:11][C:8]1[CH:7]=[C:3]([C:2]([O:24][C:17]2[CH:18]=[C:19]([CH:21]([CH3:22])[CH3:23])[CH:20]=[C:15]([CH:12]([CH3:14])[CH3:13])[CH:16]=2)=[CH:10][CH:9]=1)[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 57842,5-Dichlorobenzoic acidHCID 24758Sodium hydrideHCID 931043,5-Bis(1-methylethyl)phenol

Product 1

HCID 202989673-Chloro-6-(3,5-diisopropylphenoxy)benzoic AcidYield 49.4%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2,5-dichlorobenzoic acid (5 g) and 3,5-diisopropylphenol (4.66 g) were dissolved in dry xylene and the solution placed under dry oxygen-free nitrogen. Sodium hydride (1.25 g) was added as a suspension in petroleum ether. Cuprous bromide was added and the solution refluxed for 5 hours and cooled. The xylene was removed by low pressure distillation. The remaining solid was acidified with dilute hydrochloric acid and extracted with diethyl ether. The ethereal layer was separated, dried and distilled under low pressure to give an oil. The oil was dissolved in petroleum ether (30°-40° ). Standing gave a crystalline solid, which was recrystallised from hexane to give the title compound (4.3 g), mp 129°-130° C.

Workup

  1. temperaturethe solution refluxed for 5 hours
  2. temperaturecooled
  3. customThe xylene was removed by low pressure distillation
  4. extractionextracted with diethyl ether
  5. customThe ethereal layer was separated
  6. customdried
  7. distillationdistilled under low pressure
  8. customto give an oil
  9. customStanding gave a crystalline solid, which
  10. customwas recrystallised from hexane

Sources & evidence

ORD record
ord-c41674c889ed47979e95692495323db8
Source dataset
uspto-grants-1980_12
Patent number
US04242121

Linked notes

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