Acetic Anhydride → 6-(Acetyloxy)-2-naphthalenecarboxylic acid

HRID 1581449Notes

Reaction equation

HRID 1581449 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]2.[C:15](OC(=O)C)(=[O:17])[CH3:16]>S(=O)(=O)(O)O.O>[C:15]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]2)(=[O:17])[CH3:16]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 855576-Hydroxy-2-naphthoic acid

Product 1

HCID 870386-(Acetyloxy)-2-naphthalenecarboxylic acidYield 99%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Procedure

25 Grams (133 mmol) of 6-hydroxy-2-naphthoic acid and 68 g (265 mmol) of acetic anhydride were placed in a reactor, and while the mixture was stirred, 0.05 g of concentrated sulfuric acid was added. The mixture was stirred until heat generation ceased, and the mixture was further heated and stirred at 80° C. for 1 hour and then gradually cooled to room temperature. While the reaction mixture was cooled in an ice bath, 500 g of water was gradually added, and the mixture was stirred at room temperature for 3 hours to quench unreacted acetic anhydride. A precipitated white solid was recovered by filtration, washed with water to remove acetic acid, and dried with a vacuum dryer, to give 30.3 g of an end compound (yield 99%)

Workup

  1. stirringThe mixture was stirred
  2. temperatureuntil heat generation
  3. temperaturethe mixture was further heated
  4. stirringstirred at 80° C. for 1 hour
  5. temperatureWhile the reaction mixture was cooled in an ice bath
  6. stirringthe mixture was stirred at room temperature for 3 hours
  7. customto quench unreacted acetic anhydride
  8. filtrationA precipitated white solid was recovered by filtration
  9. washwashed with water
  10. customto remove acetic acid
  11. customdried with a vacuum dryer

Sources & evidence

ORD record
ord-f97836bbd0c64e2c8d8e207653046f63
Source dataset
uspto-grants-2004_05
Patent number
US06730371B2

Reaction notes

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