1,4-Butanediol → 4-Nonyloxybutanol

HRID 439748

Reaktionsgleichung

Reaktionsgleichung von HRID 439748
[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][OH:5].[H-].[Na+].Br[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>CN(C)C=O>[CH2:10]([O:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:6])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Komponenten

5

Edukt 3

HCID 80641,4-ButanediolHCID 127421-BromononaneHCID 24758Sodium hydride

Produkt 1

HCID 224079404-Nonyloxybutanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 7.1 ml of 1,4-butanediol in 40 ml of dimethylformamide, 1.8 gms of sodium hydride are added; and the reaction mixture is stirred at room temperature for 15 minutes. To this solution is added 7.6 ml of bromononane and the reaction mixture is stirred at room temperature for 44 hours. The reaction mixture is then partitioned between ethyl acetate and water and the organic layer is washed with brine, dried over sodum sulfate, filtered, and concentrated under vacuum. The residue is flash chromatographed with an 8/1 ratio of ethyl acetate and hexane to give 4-nonyloxybutanol as a clear colorless liquid.

Aufarbeitung

  1. stirringthe reaction mixture is stirred at room temperature for 44 hours
  2. customThe reaction mixture is then partitioned between ethyl acetate and water
  3. washthe organic layer is washed with brine
  4. dry with materialdried over sodum sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customchromatographed with an 8/1 ratio of ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-dcffb15bac664b1680da6a2bfc1e2717
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05516767

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