Water → 4-Tetradecyloxybenzyl alcohol

HRID 235701

Reaktionsgleichung

Reaktionsgleichung von HRID 235701
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([O-])=[O:27])=[CH:24][CH:23]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].O.[OH-].[Na+]>O1CCCC1>[CH2:7]([O:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:26][OH:27])=[CH:29][CH:30]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 200435124-TetradecyloxybenzoateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 100873844-Tetradecyloxybenzyl alcoholAusbeute 75,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To about 13.61 g of lithium aluminum hydride in about 200 ml of tetrahydrofuran was added, over about 1/2 hour, a solution of about 130 g of 4-tetradecyloxybenzoate in about 400 ml of tetrahydrofuran, in an ice bath with stirring and maintaining the temperature below about 40° C. After stirring about 2 hours the mixture was cooled to about 0° C., about 9 ml of water was added dropwise followed by the dropwise addition of about 18 ml of about 15% sodium hydroxide and about 30 ml of water. This mixture was filtered through celite, the solvent was removed and the residue recrystallized from ethanol, giving about 94.5 g of the desired title compound as a white solid, mp 75°-76° C.

Aufarbeitung

  1. temperaturemaintaining the temperature below about 40° C
  2. filtrationThis mixture was filtered through celite
  3. customthe solvent was removed
  4. customthe residue recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-ce3c53ea81fa4bcfab8cfcb2a31ca06c
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04640913

Verknüpfte Notizen

Wird geladen…