Reaction #2453

ord-83277f5bcbe3453880c179fb06727b5a

Reaction equation

O=C(O)c1ccc(O)cc1F
2-fluoro-4-hydroxybenzoic acid
CC(=O)OC(C)=O
acetic anhydride
→
CC(=O)Oc1ccc(C(=O)O)c(F)c1
4-acetoxy-2-fluorobenzoic acid

Reactants

O=C(O)c1ccc(O)cc1F
2-fluoro-4-hydroxybenzoic acid
CC(=O)OC(C)=O
acetic anhydride

Reagents

O=S(=O)(O)O
sulfuric acid

Solvents

O
water
O
water

Conditions

Temperature
80°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONmixed
  2. 2
    workup.ADDITIONwas added
  3. 3
    Otherprecipitated crystal
  4. 4
    Filtrationwas recovered by filtration
  5. 5
    OtherThe crystal was dried under vacuum

Procedure

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

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05728864uspto-grants-1998_03