(RS)-Naproxen methyl ester → 2-(6-Methoxy-2-naphthyl)propionic acid

HRID 1907009Notes

Reaction equation

HRID 1907009 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]([CH3:18])[C:14]([O:16]C)=[O:15])[CH:7]=[CH:6]2.CO.[OH-].[K+].O>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]([CH3:18])[C:14]([OH:16])=[O:15])[CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 529084(RS)-Naproxen methyl esterHCID 86591755KOH MeOH Water

Product 1

HCID 13022-(6-Methoxy-2-naphthyl)propionic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The crude methyl 2-(6-methoxy-2-naphthyl)propionate is hydrolyzed with methanol/potassium hydroxide/water until TLC indicates no remaining ester. Then the reaction mixture is poured into water and extracted with methylene chloride and acidified with hydrochloric acid. The mixture is filtered and the organic and aqueous layers are separated. The aqueous layer then is acidified and filtered to yield 13.5 g of 2-(6-methoxy-2-naphthyl)propionic acid (melting point: 153°-155° C.).

Workup

  1. extractionextracted with methylene chloride
  2. filtrationThe mixture is filtered
  3. customthe organic and aqueous layers are separated
  4. filtrationfiltered

Sources & evidence

ORD record
ord-edbe59e1af634d45ae4507ea27f0ab33
Source dataset
uspto-grants-1987_03
Patent number
US04654438

Reaction notes

Loading…