Triethylamine → 2-Propenoic acid, 2-methyl-, (9Z)-9-octadecen-1-yl ester

HRID 1359188

Reaktionsgleichung

Reaktionsgleichung von HRID 1359188
[CH2:1]([OH:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:20](Cl)(=[O:24])[C:21]([CH3:23])=[CH2:22].C(N(CC)CC)C>C(Cl)Cl>[C:20]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])(=[O:24])[C:21]([CH3:23])=[CH2:22]

Komponenten

5

Edukt 3

HCID 8471Triethylamine2×HCID 13528Methacryloyl chlorideHCID 5284499Oleyl Alcohol2×

Produkt 1

HCID 64363902-Propenoic acid, 2-methyl-, (9Z)-9-octadecen-1-yl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Oleyl alcohol (26.8 grams) is placed in a three-neck flask under a blanket of nitrogen. The entire reaction contents are cooled in an ice bath. Methacryloyl chloride (10.5 grams) dissolved in about 50 mL of methylene chloride is added slowly to the cooled oleyl alcohol with vigorous stirring in about 2 hours. Triethylamine (11.5 g) dissolved in 25 mL of methylene chloride is subsequently added in about an hour. After addition of triethylamine, the solution is allowed to warm to ambient temperature and is stirred for another 4 hours in order to complete the reaction. The precipitated triethylammonium chloride is removed by filtration, and the filtrate is washed with brine solution (saturated NaCl) followed by washings with dil. NaOH and dil. HCl. The organic layer is dried with anhydrous magnesium sulfate and the solvent is removed in vacuo to yield oleyl methacrylate in good yields. Oleyl methacrylate is stabilized from polymerization by addition of approximately 10 ppm hydroquinone. The structure of the product is verified by 1H and 13C NMR spectroscopy.

Aufarbeitung

  1. customThe entire reaction contents
  2. temperatureare cooled in an ice bath
  3. additionis subsequently added in about an hour
  4. stirringis stirred for another 4 hours in order
  5. customthe reaction
  6. customThe precipitated triethylammonium chloride is removed by filtration
  7. washthe filtrate is washed with brine solution (saturated NaCl)
  8. washfollowed by washings with dil. NaOH and dil. HCl
  9. dry with materialThe organic layer is dried with anhydrous magnesium sulfate
  10. customthe solvent is removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-99fa5711c57a48ab9fd8bf0ed52e646b
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06599972B2

Verknüpfte Notizen

Wird geladen…