Stearyl Alcohol → n-Octadecyl Sorbate

HRID 1594538Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1594538
[C:1](Cl)(=[O:7])/[CH:2]=[CH:3]/[CH:4]=[CH:5]/[CH3:6].[CH2:9]([OH:27])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>C1COCC1>[C:1]([O:27][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])(=[O:7])/[CH:2]=[CH:3]/[CH:4]=[CH:5]/[CH3:6]

Komponenten

4

Edukt 2

HCID 8221Stearyl AlcoholHCID 5368941(2E,4E)-hexa-2,4-dienoyl chloride

Produkt 1

HCID 22034995n-Octadecyl Sorbate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 0.9 g (6.9 mmol) of sorboyl chloride in 6 mL of THF was added slowly with stirring to a mixture of 1.87 g (6.9 mmol) of n-octadecanol in 10 mL of THF at 40° C. The resulting mixture was refluxed for 16 hours. The solvent was evaporated under reduced pressure and the crude product was purified by column chromatography on silica gel using chloroform as eluent. The appropriate fractions were combined and evaporated to dryness in vacuo to give a white solid product: 1.04 g (42%) yield. TLC (CHCl3)Rf=0.75. 1H NMR (300 MHz) δ 0.89 [3H, t, —(CH3)15CH3)],1.25 [30H, br m, —(CH3)15—], 1.62 [2H, t, —OCH2CH2—], 1.86 [3H, d, CH3CH═], 4.14 [2H, t, —OCH2—], 5.79 [1H, d, OCCH═], 6.19 [2H, m, CH3CH═CH—], 7.22 [1H, m, CH3CH═CH—CH═].

Aufarbeitung

  1. temperatureThe resulting mixture was refluxed for 16 hours
  2. customThe solvent was evaporated under reduced pressure
  3. customthe crude product was purified by column chromatography on silica gel
  4. customevaporated to dryness in vacuo
  5. customto give a white solid product
  6. custom1.04 g (42%) yield

Quellen und Nachweise

ORD-Eintrag
ord-d4181062663045829912cc311a1e2401
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06284258B1

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