Hydrochloric Acid → 4-Acetoxy-2-fluorobenzoic acid

HRID 234576Notes

Reaction equation

HRID 234576 reaction equation
[OH-].[K+].[F:3][C:4]1[CH:12]=[C:11]([OH:13])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7].[C:14](OC(=O)C)(=[O:16])[CH3:15].Cl>O>[F:3][C:4]1[CH:12]=[C:11]([O:13][C:14](=[O:16])[CH3:15])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 14797Potassium HydroxideHCID 27833982-Fluoro-4-hydroxybenzoic Acid

Product 1

HCID 227214164-Acetoxy-2-fluorobenzoic acidYield 62.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

In a 100 ml-reaction vessel, 12.1 g (1.83×10-1M) of potassium hydroxide and 50 ml of water were placed, followed by cooling to 0° C. To the mixture, 12.0 g (7.69×10-2M) of 2-fluoro-4-hydroxybenzoic acid was added and dissolved therein. To the solution, 7.9 g (7.74×10-2M) of acetic anhydride was added dropwise in 30 minutes at 0° C., followed by stirring for 2 hours. After stirring, the reaction mixture was acidified with 6N-hydrochloric acid to precipitate a crystal. The crystal was recovered by filtration, followed by washing with water and drying to obtain 9.5 g of 2-fluoro-4-acetoxybenzoic acid (Yield: 62.4%).

Workup

  1. dissolutiondissolved
  2. stirringAfter stirring
  3. customto precipitate a crystal
  4. filtrationThe crystal was recovered by filtration
  5. washby washing with water
  6. customdrying

Sources & evidence

ORD record
ord-8dcf205b41c142fa875fb34c962140db
Source dataset
uspto-grants-1997_01
Patent number
US05595685

Reaction notes

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