Water → 3-(2-Phenylethoxy)propanoic acid

HRID 963564Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 963564
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[C:22]1([CH2:28][CH2:29][O:30][CH2:31][CH2:32][CH2:33][OH:34])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(CC2OCCC[O:43]2)C=CC=CC=1.O>CN(C=O)C>[C:22]1([CH2:28][CH2:29][O:30][CH2:31][CH2:32][C:33]([OH:43])=[O:34])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 796012-Benzyl-1,3-dioxaneHCID 2724130Cornforth reagentHCID 190822593-(2-Phenylethoxy)propan-1-ol

Produkt 1

HCID 154386723-(2-Phenylethoxy)propanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Pyridinium dichromate (100 g) was added to a solution of 3-[2-phenylethoxy]-propanol (13.6 g) (prepared from 2-phenylmethyl-1,3-dioxane following the method described in Can. J. Chem., 1974, 52, 888) in DMF (400 ml). The whole was rapidly stirred for 6 hours at which point water was added. This was then extracted with ether (×3). The combined ethereal layers were extracted with 10% aqueous sodium hydroxide solution (500 ml). The basic solution was made acidic pH 1-2 with concentrated hydrochloric acid and extracted with ether. These ethereal extracts were then combined, washed with brine, dried (MgSO4) and evaporated under reduced pressure to yield the subtitled compound (7.6 g).

Aufarbeitung

  1. additionwas added
  2. extractionThis was then extracted with ether (×3)
  3. extractionThe combined ethereal layers were extracted with 10% aqueous sodium hydroxide solution (500 ml)
  4. extractionextracted with ether
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-750a172989934704ac87af85f4235205
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05763465

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