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

HRID 2413373Notes

Reaction equation

HRID 2413373 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.C(Cl)(Cl)Cl.Cl.C(COC)OC>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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 80711,2-DimethoxyethaneHCID 529084(RS)-Naproxen methyl ester

Product 1

HCID 13022-(6-Methoxy-2-naphthyl)propionic acidYield 57.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 90 mg (0.37 mmol) of methyl (+)-α-(6-methoxy-2-naphthyl)propionate having a 100% optical purity [α]D20 +78.2° (CHCl3)], 1 ml of 12N aqueous hydrochloric acid and 1 ml of dimethoxyethane was stirred at 50° C. for 23 hours. After adding 10 ml of water, the mixture was extracted with diethyl ether (8 ml×3), and the extract was washed with water (3 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by column chromatography [silica gel, hexane+ethyl acetate (1:2)] to obtain 49 mg of (+)-α-(6-methoxy-2-naphthyl)propionic acid as colorless crystals. Yield, 63%.

Workup

  1. extractionthe mixture was extracted with diethyl ether (8 ml×3)
  2. washthe extract was washed with water (3 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by column chromatography [silica gel, hexane+ethyl acetate (1:2)]

Sources & evidence

ORD record
ord-b42c26040e64461581dc11e885a68824
Source dataset
uspto-grants-1985_01
Patent number
US04496755

Reaction notes

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