Reaktionsgleichung
[CH2:1]([OH:16])[CH:2]([OH:15])[CH2:3][O:4][CH2:5][CH:6]([OH:14])[CH2:7][O:8][CH2:9][CH:10]([OH:13])[CH2:11][OH:12].C(O)C(O)COCC(O)CO.[CH:28](=O)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>[Pd]>[CH2:28]([O:12][CH2:11][CH:10]([OH:13])[CH2:9][O:8][CH2:7][CH:6]([OH:14])[CH2:5][O:4][CH2:3][CH:2]([OH:15])[CH2:1][OH:16])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
The procedure of Example 1 is repeated, except 168.2 g (0.70 mol) of triglycerol from Solvay is used in place of diglycerol, 21.88 g (0.14 mol) of decanal is used in place of nonanal, and 1.1 g of 5% Pd/C is used in place of 1.03 g of 5% Pd/C. After the reaction completion, the product is extracted with diethyl ether (30 mL×7). The solvent is evaporated and a half of the crude product is chromatographed on silica gel using straight ethyl acetate. Appropriate fractions are combined, solvent evaporated to give 8.01 g of the product as a mixture of isomers. 1H NMR (δ, CDCl3, ppm): 0.88 t (3 H, CH3), 1.26 (14 H, (CH2)7), 1.58 t (2 H, CH2), 3.4-4.2 m (21 H, triglycerol moiety+CH2O+OH groups). 13C NMR (δ, CDCl3, ppm): 14.44, 23.02, 26.41, 29.64, 29.80, 29.90, 29.93, 32.20, 29.96, 64.15 (decyl), 69.82, 69.88, 71.04, 71.13, 71.99, 72.01, 72.03, 72.06, 73.24, 73.28, 73.32, 73.36 (triglycerol). GS/MS with TMS derivatization: 668 (MW+four TMS groups).
Aufarbeitung
- extractionAfter the reaction completion, the product is extracted with diethyl ether (30 mL×7)
- customThe solvent is evaporated
- customa half of the crude product is chromatographed on silica gel using straight ethyl acetate
- customsolvent evaporated
Quellen und Nachweise
- ORD-Eintrag
- ord-2c4697d494834733a52a02e77136c54d
- Quelldatensatz
- uspto-grants-2015_04
- Patentnummer
- US08999071B2
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