Water → 3,7-Dimethyl-4-hydroxy-6-octen-1-ol

HRID 1447533

Reaktionsgleichung

Reaktionsgleichung von HRID 1447533
[CH3:1][CH:2]([C:8](=[O:14])[CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12])[CH2:3][C:4](OC)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(=O)(O)[O-].[Na+].O>CCOCC.C(OCC)(=O)C>[CH3:1][CH:2]([CH:8]([OH:14])[CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12])[CH2:3][CH2:4][OH:5]

Komponenten

7

Edukt 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 15340230Methyl 3,7-dimethyl-4-oxo-6-octenoateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 136688813,7-Dimethyl-4-hydroxy-6-octen-1-olAusbeute 863,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Methyl 3,7-dimethyl-4-oxo-6-octenoate (68 g, 34 mmole) in ether (10 ml) is added to a mixture of lithium aluminum hydride (1.3 g, 34 mmole) and ether (150 ml) at 0°. After the addition is complete the mixture is allowed to warm to room temperature and stirred for 1 hour, after which it is cooled to 0° and carefully added to a 5% aqueous sodium bicarbonate solution (50 ml). The resulting mixture is treated with water (100 ml) and ethyl acetate (300 ml). The organic phase is separated, dried (Na2SO4) and the solvent is removed in vacuo to give a colorless oil (50.6 g, 94%). This material shows one spot on TLC (silica gel 50% ethyl acetate in hexane) and is not further purified.

Aufarbeitung

  1. additionAfter the addition
  2. temperatureafter which it is cooled to 0°
  3. customThe organic phase is separated
  4. dry with materialdried (Na2SO4)
  5. customthe solvent is removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-04b9519738864607bff2991fffc6662f
Quelldatensatz
uspto-grants-1979_12
Patentnummer
US04177194

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