Sodium Hydroxide → 2,6-dichloro-4-(trifluoromethyl)benzoic Acid

HRID 2256911Notes

Reaction equation

HRID 2256911 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[C:11]([Cl:19])[C:5]=1[C:6]([O:8]CC)=[O:7]>O.C(O)C>[Cl:3][C:4]1[CH:14]=[C:13]([C:15]([F:16])([F:17])[F:18])[CH:12]=[C:11]([Cl:19])[C:5]=1[C:6]([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 54315306Ethyl 2,6-dichloro-4-(trifluoromethyl)benzoate

Product 1

HCID 116804602,6-dichloro-4-(trifluoromethyl)benzoic AcidYield 71.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium hydroxide (41.6 g) in water was added to a solution of ethyl 2,6-dichloro-4-trifluoromethylbenzoate (96.3 g) in ethanol. The mixture was heated at reflux for 2.5 hours then cooled and evaporated. It was diluted with water and extracted with ether. The aqueous layer was acidified to pH1 and extracted with ether, washed with water, dried (Na25O4) and filtered. The filtrate was evaporated to dryness and the residue was triturated with n-hexane and filtered to give 2.6-dichloro-4-trifluoromethylbenzoic acid (62.3 g) as a white solid mp 138.5°-139° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2.5 hours
  3. temperaturethen cooled
  4. customevaporated
  5. additionIt was diluted with water
  6. extractionextracted with ether
  7. extractionextracted with ether
  8. washwashed with water
  9. customdried (Na25O4)
  10. filtrationfiltered
  11. customThe filtrate was evaporated to dryness
  12. customthe residue was triturated with n-hexane
  13. filtrationfiltered

Sources & evidence

ORD record
ord-e351222a5cdf462ebe54aa6449df0f61
Source dataset
uspto-grants-1997_08
Patent number
US05656573

Reaction notes

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