Water → 3,3-Dimethylpentane-1,5-diol

HRID 396251

Reaktionsgleichung

Reaktionsgleichung von HRID 396251
[CH3:1][C:2]1([CH3:10])[CH2:8][C:7](=O)[O:6][C:4](=[O:5])[CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH3:1][C:2]([CH3:10])([CH2:8][CH2:7][OH:6])[CH2:3][CH2:4][OH:5]

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 778133,3-Dimethylglutaric anhydrideHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 128107743,3-Dimethylpentane-1,5-diol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 3,3-dimethylglutaric anhydride in dry THF (60 cm3) was added over 30 min. to lithium aluminum hydride in dry THF (300 cm3) under nitrogen at 0° C. The mixture was then brought gradually up-to reflux. After 3 h, the mixture was cooled, treated with water (3.3 cm3), sodium hydroxide solution (15%, 3.3 cm3) and water (9.9 cm3). The mixture was then filtered, the precipitate extracted with EtOAc (×3), and the combined organics evaporated to afford 3,3-dimethyl-1,5-pentanediol (quantitative yield); 1H NMR (CDCl3) δ 0.95 (s, 6H), 1.57 (t, 4H, J=6.3 Hz), 3.75 (t, 4H, J−6.3 Hz).

Aufarbeitung

  1. temperatureThe mixture was then brought gradually up-to reflux
  2. temperaturethe mixture was cooled
  3. filtrationThe mixture was then filtered
  4. extractionthe precipitate extracted with EtOAc (×3)
  5. customthe combined organics evaporated

Quellen und Nachweise

ORD-Eintrag
ord-4bf78c2ff31c4cd889bd8b0babe0984d
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06608068B2

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