Sulfuric Acid → 4-Acetoxy-3-fluorobenzoic acid

HRID 1589725Notes

Reaction equation

HRID 1589725 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[F:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[OH:18])[C:12]([OH:14])=[O:13].S(=O)(=O)(O)O>S(=O)(=O)(O)O.O>[C:1]([O:18][C:17]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=1[F:8])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 1604563-Fluoro-4-hydroxybenzoic acid

Product 1

HCID 193653054-Acetoxy-3-fluorobenzoic acidYield 79.4%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Procedure

6.40 ml of acetic anhydride was added to 5.00 g (32.00 mM) of 3-fluoro-4-hydroxybenzoic acid. Under stirring at room temperature, two drops of concentrated sulfuric acid was added thereto (the mixture solidified as soon as the concentrated sulfuric acid was added), followed by heat-stirring for 10 minutes at 107°-111° C. on an oil bath (the mixture became transparent and melted by heating). After the reaction, the reaction mixture was poured into 150 ml of iced water to precipitate a crystal. The crystal was recovered by filtration and recrystallized from 20 ml of methanol to obtain 5.04 g of 4-acetoxy-3-fluorobenzoic acid (Yield: 79.4%).

Workup

  1. additionwas added),
  2. stirringby heat-stirring for 10 minutes at 107°-111° C. on an oil bath (the mixture
  3. temperatureby heating)
  4. customAfter the reaction
  5. customto precipitate a crystal
  6. filtrationThe crystal was recovered by filtration
  7. customrecrystallized from 20 ml of methanol

Sources & evidence

ORD record
ord-3add03f0ea2449c1a6a8cd77fef9943d
Source dataset
uspto-grants-1993_04
Patent number
US05200109

Reaction notes

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