Hydrochloric Acid → 2-(6-Methoxy-2-naphthyl)propionic acid

HRID 840036Notes

Reaction equation

HRID 840036 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([CH:15]([CH3:20])[C:16]([O:18]C)=[O:17])[CH:9]=[CH:8]2.Cl>CO>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([CH:15]([CH3:20])[C:16]([OH:18])=[O:17])[CH:9]=[CH:8]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 529084(RS)-Naproxen methyl ester

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 20 g. of sodium hydroxide and 400 ml. of methanol are added 24.5 g. of methyl 6-methoxy-2-naphthyl-α-methylacetate. The resulting reaction mixture is heated to 60° C for 5 hours. The cooled mixture is neutralized by the addition of aqueous 1N hydrochloric acid and extracted with methylene chloride. The extracts are combined, washed with water to neutrality, dried over sodium sulfate, filtered, and evaporated to give 6-methoxy-2-naphthyl-α-methylacetic acid.

Workup

  1. additionTo a mixture of 20 g
  2. customThe resulting reaction mixture
  3. extractionextracted with methylene chloride
  4. washwashed with water to neutrality
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-e5e333caecbb43f6a490e2d0ca6fd45b
Source dataset
uspto-grants-1978_06
Patent number
US04097674

Reaction notes

Loading…