Hydrochloric Acid → 2,5-Dichloro-3-fluoro-4-methylbenzoic acid

HRID 34587Notes

Reaction equation

HRID 34587 reaction equation
[Cl:1][C:2]1[C:11]([F:12])=[C:10]([CH3:13])[C:9]([Cl:14])=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[K+].Cl>CCO>[Cl:1][C:2]1[C:11]([F:12])=[C:10]([CH3:13])[C:9]([Cl:14])=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 21298239Methyl 2,5-dichloro-3-fluoro-4-methylbenzoate

Product 1

HCID 136574482,5-Dichloro-3-fluoro-4-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The diazonium salt is heated under dry conditions in a glass flask. When the reaction has ended, the crude methyl 2,5-dichloro-3-fluoro-4-methylbenzoate is taken up in 100 ml of 50% strength EtOH, and 8.2 g of KOH are added. The mixture is boiled under reflux for 1 hour and, after cooling to room temperature, is acidified with HCl. The benzoic acid which has precipitated is isolated, dried and recrystallized from toluene. Yield: 11.3 g, melting point 195°-6°.

Workup

  1. additionare added
  2. temperatureunder reflux for 1 hour
  3. customThe benzoic acid which has precipitated
  4. customis isolated
  5. customdried
  6. customrecrystallized from toluene

Sources & evidence

ORD record
ord-9572f93b969747b3a7fe4cbc771974db
Source dataset
uspto-grants-1988_08
Patent number
US04762844

Reaction notes

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