Octadecanoic acid, 1,1'-anhydride → Matairesinol stearate

HRID 490783

Reaktionsgleichung

Reaktionsgleichung von HRID 490783
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:10][C@@H:11]2[C@@H:16]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([OH:26])=[C:22]([O:24][CH3:25])[CH:23]=3)[C:14](=[O:15])[O:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[OH:9].[C:27]([O:46]C(=O)CCCCCCCCCCCCCCCCC)(=[O:45])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:10][C@@H:11]2[C@@H:16]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([OH:26])=[C:22]([O:24][CH3:25])[CH:23]=3)[C:14](=[O:15])[O:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[OH:9].[C:27]([O-:46])(=[O:45])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]

Komponenten

4

Edukt 2

HCID 69485Octadecanoic acid, 1,1'-anhydrideHCID 119205(-)-Matairesinol

Produkt 1

HCID 86597910Matairesinol stearate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

Matairesinol (500 mg, 1.4 mmol) was dissolved in 25 ml pyridine. To the solution stearic acid anhydride (3.1 g, 5.6 mmol) was added in small portions. The temperature was raised to 65° C. and the mixture was stirred for 24 h. The solvent was removed under reduced pressure and the residue dissolved in dichloromethane. Unreacted stearic anhydride and stearic acid precipitated from the dichloromethane solution and were filtered off. The solvent was then removed and the residue was washed with n-hexane to afford matairesinol stearate as a white solid. Yield 514 mg, 41%. Purity approximately 90%, consisting of some free stearic acid and acid anhydride (NMR).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in dichloromethane
  3. customprecipitated from the dichloromethane solution
  4. filtrationwere filtered off
  5. customThe solvent was then removed
  6. washthe residue was washed with n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-13e1612062ca4308948fb1b75f011120
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528166B2

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