Hydrochloric Acid → 3-Chloro-2-fluoro-5-(trifluoromethyl)benzoic acid

HRID 2193986Notes

Reaction equation

HRID 2193986 reaction equation
[Cl:1][C:2]1[C:3]([F:14])=[C:4]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[CH:5]=[O:6].[Mn]([O-])(=O)(=O)=[O:16].[K+].Cl.C(Cl)Cl>CC(C)=O.O>[Cl:1][C:2]1[C:3]([F:14])=[C:4]([CH:7]=[C:8]([C:10]([F:12])([F:13])[F:11])[CH:9]=1)[C:5]([OH:16])=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 516875Potassium PermanganateHCID 7363363-Chloro-2-fluoro-5-(trifluoromethyl)benzaldehyde

Product 1

HCID 27737513-Chloro-2-fluoro-5-(trifluoromethyl)benzoic acidYield 95.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of 3-chloro-2-fluoro-5-trifluoromethyl-benzaldehyde (1.0 g, 4.41 mmol) in acetone (15 ml) and water (3 ml) was added potassium permanganate (0.837 g, 5.3 mmol, 1.2 equiv.) and the corresponding dark violet reaction mixture was stirred for 30 min to achieve full conversion. The solvents were removed under vacuum and the dark suspension was quenched upon addition of sodium sulfite solution (sat., 20 ml). The dark violet solid was filtered off and washed with water (10 ml). The turbid light brown mother liquor was treated with HCl (25%, 3 ml, 92.3 mmol, 20.9 equiv) adjusting the pH to 1 and CH2Cl2 (50 ml) was added. The phases were separated, the organic phase was washed with water (20 ml), whereas the aqueous phase was washed with CH2Cl2 (20 ml). The combined organic phases were dried over sodium sulfate, filtered and the solvent was exchanged under vacuum with methyl cyclohexane (35 ml). The turbid suspension was concentrated under vacuum, the white precipitate was filtered off and the crystals were dried under vacuum until weight constancy to yield the product as white crystals (1.02 g, 93.8% yield).

Workup

  1. customThe solvents were removed under vacuum
  2. customthe dark suspension was quenched upon addition of sodium sulfite solution (sat., 20 ml)
  3. filtrationThe dark violet solid was filtered off
  4. washwashed with water (10 ml)
  5. additionwas added
  6. customThe phases were separated
  7. washthe organic phase was washed with water (20 ml), whereas the aqueous phase
  8. washwas washed with CH2Cl2 (20 ml)
  9. dry with materialThe combined organic phases were dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationThe turbid suspension was concentrated under vacuum
  12. filtrationthe white precipitate was filtered off
  13. customthe crystals were dried under vacuum until weight constancy

Sources & evidence

ORD record
ord-4401f0d2c3e4411a8bc6feab52f1232b
Source dataset
uspto-grants-2012_12
Patent number
US08329939B2

Reaction notes

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