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

HRID 1706570Notes

Reaction equation

HRID 1706570 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 five hours. The cooled mixture is neutralized by the addition of aqueous 1 N 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-877e18a677314041b9f0fa8772987157
Source dataset
uspto-grants-1980_06
Patent number
US04207241

Reaction notes

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