Methyl 12-hydroxystearate → Hydroxystearyl alcohol

HRID 1093

Reaktionsgleichung

Reaktionsgleichung von HRID 1093
[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH:7][CH:8]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19](OC)=[O:20].[OH-].[K+]>O1CCCC1>[CH2:19]([OH:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH:8]([OH:7])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Komponenten

5

Edukt 3

HCID 8840Methyl 12-hydroxystearateHCID 14797Potassium HydroxideHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 95421Hydroxystearyl alcoholAusbeute 86,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A 5-liter flask equipped with a stirrer, dropping funnel and reflux tube was charged with 28.5 g (0.75 mol) of LiAlH4 and 2 liters of tetrahydrofuran, to which a solution of 237.0 g (0.75 mol) of methyl 12-hydroxyoctadecanate in 1 liter of tetrahydrofuran was added dropwise over 5 hours with stirring. After completion of the dropping, the stirring was continued further for 1 hour at 65° C. After the reaction mixture was then cooled, 90 ml of a 5% aqueous solution of KOH were added with stirring. A salt precipitated was separated by filtration, and the resultant solution was concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel, thereby obtaining 185.7 g (yield: 86.6%) of 1,12-octadecanediol.

Aufarbeitung

  1. customA 5-liter flask equipped with a stirrer
  2. temperaturereflux tube
  3. additionwas added dropwise over 5 hours
  4. temperatureAfter the reaction mixture was then cooled
  5. stirringwith stirring
  6. customA salt precipitated
  7. customwas separated by filtration
  8. concentrationthe resultant solution was concentrated under reduced pressure
  9. customThe resulting residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-9598dbc5228f4c2bae79065911c76e2b
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723497

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