37414-52-1 → 2-(6-Methoxy-2-naphthyl)propionic acid

HRID 1975530Notes

Reaction equation

HRID 1975530 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]([CH3:16])[CH2:14][OH:15])[CH:7]=[CH:6]2.I([O-])(=O)(=O)=[O:18].[Na+]>C(Cl)(Cl)(Cl)Cl.C(#N)C.O.O.[Ru](Cl)(Cl)Cl>[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]([CH3:16])[C:14]([OH:18])=[O:15])[CH:7]=[CH:6]2

Participants

7

Reactant 2

HCID 3334137414-52-1HCID 23667635Sodium periodate

Product 1

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

Reagents, catalysts & solvents 4

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 962WaterSolventHCID 5943Carbon TetrachlorideSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.21 g 2-(6-methoxy-2-naphthyl)propan-1-ol in 2 ml of carbon tetrachloride, 2 ml acetonitrile, 3 ml of water, and 0.877 g of sodium metaperiodate is added 5 mg of ruthenium trichloride hydrate. After 4 hours at ambient temperature the mixture is extracted with 4 portions of 10 ml of methylene chloride. The combined organic extracts are dried over MgSO4, filtered, and concentrated to give the product 2-(6-methoxy-2-naphthyl)propionic acid.

Workup

  1. extractionAfter 4 hours at ambient temperature the mixture is extracted with 4 portions of 10 ml of methylene chloride
  2. dry with materialThe combined organic extracts are dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9668b097365d4b2d88edaf942593ac22
Source dataset
uspto-grants-1994_02
Patent number
US05286902

Reaction notes

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