Reaction #321758

Reaction equation

hydrochloric acid

2-fluoro-4-hydroxybenzoic acid

potassium hydroxide

acetic anhydride

→

2-fluoro-4-acetoxybenzoic acid

Yield 62.4%

Solvents

water

Conditions

Workup

1. 1
   workup.DISSOLUTIONdissolved
2. 2
   workup.STIRRINGAfter stirring
3. 3
   Otherto precipitate a crystal
4. 4
   FiltrationThe crystal was recovered by filtration
5. 5
   Washby washing with water
6. 6
   Otherdrying

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%).

Source