Water → 4-Chloro-2-fluorobenzoic acid

HRID 648286

Reaction equation

HRID 648286 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH3:9].[O-:10][Mn](=O)(=O)=O.[K+].[OH2:16]>>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:10])=[O:16]

Participants

4

Reactant 3

HCID 962WaterHCID 516875Potassium PermanganateHCID 5206304-Chloro-2-fluorotoluene

Product 1

HCID 991524-Chloro-2-fluorobenzoic acid

Procedure

A mixture of 2-fluoro-4-chlorotoluene (25.05 g), KMnO4 (55.04 g) and water (400 ml) is heated to reflux for about 5 hr. The reaction is then worked up by filtering while hot through Celite and the filtrate is acidified with 2 N HCl. White crystals are filtered off, dissolved in ether and washed with water and brine, dried over sodium sulfate, filtered and evaporated to yield 2-fluoro-4-chlorobenzoic acid.

Workup

  1. temperatureis heated
  2. temperatureto reflux for about 5 hr
  3. filtrationby filtering while hot through Celite
  4. filtrationWhite crystals are filtered off
  5. dissolutiondissolved in ether
  6. washwashed with water and brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-fe95aca8fcee4fd08b57c1ccc7c845a0
Source dataset
uspto-grants-1983_10
Patent number
US04411912

Linked notes

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