Acetic Acid → 4-Acetoxy-2-fluorobenzoic acid

HRID 611950Notes

Reaction equation

HRID 611950 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12](O)(=[O:14])[CH3:13]>S(=O)(=O)(O)O.O>[F:1][C:2]1[CH:10]=[C:9]([O:11][C:12](=[O:14])[CH3:13])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 27833982-Fluoro-4-hydroxybenzoic Acid

Product 1

HCID 227214164-Acetoxy-2-fluorobenzoic acid

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

4.3 Grams of 2-fluoro-4-hydroxybenzoic acid and 8.4 g of anhydrous acetic acid were placed in a two-necked flask, and mixed. While the mixture was cooled with water, 5 drops of sulfuric acid were added. After heat generation terminated, the mixture was heated at 80° C. for 30 minutes. Then, the reaction mixture was poured into cold water, and a precipitated crystal was recovered by filtration. The crystal was vacuum-dried and used in the next step. The yield of the crystal was 4.7 g.

Workup

  1. additionmixed
  2. additionwere added
  3. temperatureAfter heat generation
  4. customterminated
  5. additionThen, the reaction mixture was poured into cold water
  6. filtrationa precipitated crystal was recovered by filtration
  7. customThe crystal was vacuum-dried

Sources & evidence

ORD record
ord-6b1c7bfea1884e9690056e37454fb235
Source dataset
uspto-grants-1999_12
Patent number
US06002042

Reaction notes

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