Benzyl Chloride → 1-Benzyloxy-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraene

HRID 1262950Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1262950
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][C:10]([CH2:14][CH2:15][CH:16]=[C:17]([CH3:29])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:28])[CH2:22][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])=[CH:11][CH2:12][OH:13].[OH-].[K+]>CCCCCC>[CH2:1]([O:13][CH2:12][CH:11]=[C:10]([CH3:9])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:29])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:28])[CH2:22][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 7503Benzyl ChlorideHCID 14797Potassium HydroxideHCID 65183Tetraprenol

Produkt 1

HCID 545558871-Benzyloxy-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraeneAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Versuchsvorschrift

To 100 ml of benzyl chloride were added 15 g of 3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraen-1-ol and 6.0 g of finely divided potassium hydroxide, and the resulting mixture was refluxed under stirring for 2 hours. The mixture was cooled and then to the mixture was added 1 liter of hexane. The hexane solution was then washed with water and concentrated. The concentrate was purified over a silica gel column to give 12 g of 1-benzyloxy-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraene (yield 61%).

Aufarbeitung

  1. temperaturethe resulting mixture was refluxed
  2. temperatureThe mixture was cooled
  3. washThe hexane solution was then washed with water
  4. concentrationconcentrated
  5. customThe concentrate was purified over a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-54634c1c6ef347cf8529e65e9b020cb0
Quelldatensatz
uspto-grants-1984_06
Patentnummer
US04454330

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