Methanol → Glyceryl 1,3-distearate

HRID 1259048

Reaktionsgleichung

Reaktionsgleichung von HRID 1259048
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][CH2:21][CH2:22][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.CO>CN(C)C1C=CN=CC=1.ClCCl.C(=O)([O-])O.[Na+].C(OCC)(=O)C>[C:13]([O:8][CH2:7][CH:5]([CH2:4][O:3][C:2](=[O:12])[CH2:10][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:41][CH2:40][CH3:39])[OH:9])(=[O:32])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Komponenten

9

Edukt 4

HCID 887MethanolHCID 5281Stearic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 4180364Dihydroxyacetone dimer

Produkt 1

HCID 101269Glyceryl 1,3-distearateAusbeute 33,6 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

3.0 g of dihydroxyacetone dimer, 22.7 g of stearic acid, 16.8 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride salt, and 10.8 g of 4-dimethylaminopyridine were dissolved in 100 mL of dichloromethane, for overnight reaction under agitation at ambient temperature. Adding 0.5 L of methanol to the reaction solution, the generated powder was filtered and recovered. The powder recovered by filtration was washed with methanol. After the washed powder was dried, 6 g of the dried powder was dissolved in a mixture solution of 400 mL of tetrahydrofuran and 20 mL of aqueous 10% acetic acid solution, to which 1.1 g of sodium borohydride was added in small portions at 0° C. Subsequently, the resulting mixture was agitated at ambient temperature for 6 hours to promote the reaction. The resulting reaction solution was poured in saturated aqueous sodium hydrogen carbonate, for extraction in 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 3.5 g of the intended product.

Aufarbeitung

  1. customreaction under agitation at ambient temperature
  2. filtrationthe generated powder was filtered
  3. customrecovered
  4. filtrationThe powder recovered by filtration
  5. washwas washed with methanol
  6. customAfter the washed powder was dried
  7. dissolution6 g of the dried powder was dissolved in a mixture solution of 400 mL of tetrahydrofuran and 20 mL of aqueous 10% acetic acid solution, to which 1.1 g of sodium borohydride
  8. additionwas added in small portions at 0° C
  9. customthe reaction
  10. customThe resulting reaction solution
  11. customAfter the organic layer was dried
  12. concentrationthe organic layer was concentrated under reduced pressure
  13. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-71d110c218a04a70bb1fd932f2cf64bd
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466255B2

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