1-Iodohexadecane → 2-(Benzyloxy)-3-(hexadecyloxy)propan-1-ol

HRID 235697

Reaktionsgleichung

Reaktionsgleichung von HRID 235697
[H-].[Na+].[CH2:3]([O:10][CH:11]([CH2:14][OH:15])[CH2:12][OH:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:16](I)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>CN(C)C=O>[CH2:31]([O:15][CH2:14][CH:11]([O:10][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:12][OH:13])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH3:16]

Komponenten

5

Edukt 3

HCID 110071-IodohexadecaneHCID 24758Sodium hydrideHCID 2035672-(Phenylmethoxy)-1,3-propanediol

Produkt 1

HCID 132771402-(Benzyloxy)-3-(hexadecyloxy)propan-1-olAusbeute 26,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of about 14.26 g of washed about 50% sodium hydride in about 500 ml of dimethylformamide was added about 49.2 g of 2-(benzyloxy)-1,3-propanediol over about 20 minutes. The mixture was stirred for about 40 minutes, then cooled to about 0° C. and about 95.13 g of hexadecyl iodide were added. After standing about 10 minutes, the mixture was stirred at room temperature for about 3 hours, then filtered through celite and diluted with about 1000 ml of water. This mixture was extracted with petroleum ether. The ether extract was dried and the solvent removed giving an oil. This oil was chromatographed on a column of florisil, eluting first with petroleum ether and then successively with about 5% and about 10% ether in petroleum ether to elute the product, giving about 28.8 g of the desired title compound as a light yellow oil.

Aufarbeitung

  1. waitAfter standing about 10 minutes
  2. stirringthe mixture was stirred at room temperature for about 3 hours
  3. filtrationfiltered through celite
  4. additiondiluted with about 1000 ml of water
  5. extractionThis mixture was extracted with petroleum ether
  6. extractionThe ether extract
  7. customwas dried
  8. customthe solvent removed
  9. customgiving an oil
  10. customThis oil was chromatographed on a column of florisil
  11. washeluting first with petroleum ether
  12. washsuccessively with about 5% and about 10% ether in petroleum ether to elute the product

Quellen und Nachweise

ORD-Eintrag
ord-a4eda06d550a4181ae7848f8b6d71f42
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04640913

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