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

HRID 27649

Reaktionsgleichung

Reaktionsgleichung von HRID 27649
[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-].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 769Bicarbonate IonHCID 962WaterHCID 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 sodim 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-a6daa448ebb4476396eec9aac57fc091
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04222937

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