Hydrochloric Acid → 6-(Acetyloxy)-2-naphthalenecarboxylic acid

HRID 234578Notes

Reaction equation

HRID 234578 reaction equation
[OH-].[K+].[OH:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([C:14]([OH:16])=[O:15])[CH:8]=[CH:7]2.[C:17](OC(=O)C)(=[O:19])[CH3:18].Cl>O>[C:17]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([C:14]([OH:16])=[O:15])[CH:8]=[CH:7]2)(=[O:19])[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 14797Potassium HydroxideHCID 855576-Hydroxy-2-naphthoic acid

Product 1

HCID 870386-(Acetyloxy)-2-naphthalenecarboxylic acidYield 74.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

In a 100 ml-reaction vessel, 16.7 g (2.53×10-1M) of potassium hydroxide and 85 ml of water were placed, followed by cooling to 0° C. To the mixture, 20.0 g (1.06×10-1M) of 6-hydroxy-2-naphthoic acid was added and dissolved therein. To the solution, 10.9 g (1.07×10-1M) of acetic anhydride was added dropwise in 40 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 18.3 g of 6-acetoxy-2-naphthoic acid (Yield: 74.4%).

Workup

  1. dissolutiondissolved
  2. stirringAfter stirring
  3. customto precipitate a crystal
  4. filtrationThe crystal was recovered by filtration
  5. washby washing with water
  6. customdrying

Sources & evidence

ORD record
ord-813f9efe0a874d70ae996de60db0c895
Source dataset
uspto-grants-1997_01
Patent number
US05595685

Reaction notes

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