Cetyl Alcohol → 8-(Hexadecyloxy)-7-methoxy-1-octene

HRID 35957

Reaktionsgleichung

Reaktionsgleichung von HRID 35957
[H-].[Na+].[OH:3][CH2:4][CH:5]([O:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].S(C1C=CC(C)=CC=1)([O-])(=O)=O.[CH2:25](O)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]>CN(C)C=O.O>[CH2:40]([O:3][CH2:4][CH:5]([O:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH3:25]

Komponenten

7

Edukt 4

HCID 2682Cetyl AlcoholHCID 24758Sodium hydrideHCID 85570p-ToluenesulfonateHCID 199395708-Hydroxy-7-methoxy-1-octene

Produkt 1

HCID 199395658-(Hexadecyloxy)-7-methoxy-1-octene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a suspension of 7.4 g of 60% sodium hydride in 100 ml of dimethylformamide was added a solution of 8-hydroxy-7-methoxy-1-octene in 150 ml of dimethylformamide over 1.5 hours. A 63.4 g portion of the tosylate of 1-hexadecanol was added and the mixture was stirred for 18 hours, poured into water and extracted with ether. The ether solution was dried and evaporated. The residue was purified by chromatography giving 41.5 g of the title compound as a oil.

Aufarbeitung

  1. extractionextracted with ether
  2. dry with materialThe ether solution was dried
  3. customevaporated
  4. customThe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-95f61b892d9b4419a2ca820c0f9db754
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05411983

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