Ethyl Acetate → 1,3-Diolein

HRID 1259047

Reaktionsgleichung

Reaktionsgleichung von HRID 1259047
C1O[C:5]([OH:9])([CH2:7][OH:8])[CH2:4][O:3][C:2]1([OH:12])[CH2:10]O.[C:13]([OH:32])(=O)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].Cl.C(N=C=N[CH2:39][CH2:40][CH2:41]N(C)C)C.C(O[CH2:49][CH3:50])(=O)C>CN(C)C1C=CN=CC=1.ClCCl.C(=O)([O-])O.[Na+]>[C:13]([O:8][CH2:7][CH:5]([CH2:4][O:3][C:2](=[O:12])[CH2:10][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]/[CH:17]=[CH:16]\[CH2:15][CH2:14][CH2:13][CH2:49][CH2:50][CH2:41][CH2:40][CH3:39])[OH:9])(=[O:32])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Komponenten

8

Edukt 4

HCID 8857Ethyl AcetateHCID 445639Oleic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 4180364Dihydroxyacetone dimer

Produkt 1

HCID 54971651,3-Diolein

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

3.8 g of dihydroxyacetone dimer, 25 g of oleic acid, g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride salt, and 12.9 g of 4-dimethylaminopyridine were dissolved in 150 mL of dichloromethane, for reaction under agitation at ambient temperature for 4 hours. The organic layer was washed by adding aqueous 0.5 M potassium dihydrogen phosphate solution to the reaction solution. After the organic layer was dried and concentrated under reduced pressure, 1 L of methanol was added to the resulting residue; the generated powder was filtered and recovered, and then dried. The dried powder was dissolved in a mixture solution of 170 mL of tetrahydrofuran and 17 mL of aqueous 10% acetic acid solution, to which 1.7 g of sodium borohydride was added in small portions at 0° C. Subsequently, the resulting mixture was agitated at ambient temperature for 2 hours to promote the reaction. The resulting reaction solution was poured in saturated aqueous sodium hydrogen carbonate, for extraction with ethyl acetate. After the organic layer was dried, the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, to obtain 14.5 g of the intended product.

Aufarbeitung

  1. washThe organic layer was washed
  2. additionby adding aqueous 0.5 M potassium dihydrogen phosphate solution to the reaction solution
  3. customAfter the organic layer was dried
  4. concentrationconcentrated under reduced pressure, 1 L of methanol
  5. additionwas added to the resulting residue
  6. filtrationthe generated powder was filtered
  7. customrecovered
  8. customdried
  9. dissolutionThe dried powder was dissolved in a mixture solution of 170 mL of tetrahydrofuran and 17 mL of aqueous 10% acetic acid solution, to which 1.7 g of sodium borohydride
  10. additionwas added in small portions at 0° C
  11. customthe reaction
  12. customThe resulting reaction solution
  13. customAfter the organic layer was dried
  14. concentrationthe organic layer was concentrated under reduced pressure
  15. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-77cfd525dc5047258d2e003676c05383
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466255B2

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