Solketal → 1-O-Hexadecylglycerol

HRID 456384Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 456384
C[C:2]1([CH3:9])[O:6][CH:5]([CH2:7][OH:8])[CH2:4][O:3]1.[OH-].[K+].[CH2:12](Br)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]CC>C1C=CC=CC=1.CCOCC>[CH2:2]([O:3][CH2:4][CH:5]([CH2:7][OH:8])[OH:6])[CH2:9][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][CH3:12]

Komponenten

6

Edukt 3

HCID 7528SolketalHCID 82131-BromohexadecaneHCID 14797Potassium Hydroxide

Produkt 1

HCID 727331-O-HexadecylglycerolAusbeute 77,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

D-Acetone glycerol (4 grams) for synthesis of L-ALLE or L-Acetone glycerol for synthesis of D-ALLE, powdered potassium hydroxide (approximately 10 grams) and hexadecyl bromide (9.3 grams) in benzene (100 ml) were stirred and refluxed for 5 hours, while removing the water formed by azeotropic distillation (compare W. J. Baumann and H. K. Mangold, J. Org. Chem. 29: 3055, 1964 and F. Paltauf, Monatsh. 99:1277, 1968). The volume of the solvent was gradually reduced to about 20 ml, and the resulting mixture was cooled to room temperature and dissolved in ether (100 ml). The resulting solution was washed with water (2×50 ml), and the solvent was removed under reduced pressure. A 100 ml mixture of 90:10:5 methanol:water:concentrated hydrochloric acid was added to the residue and the mixture was refluxed for 10 minutes. The product was extracted with ether (200 ml) and was washed consecutively with water (50 ml), 10% sodium hydroxide (20 ml) and again with water (volumes of 20 ml) until neutral. The solvent was removed under reduced pressure and the product (8.8 grams) was crystallized from hexane to give 7.4 grams of pure 1-hexadecyl-glyceryl ether (compound I, FIG. 1) for synthesis of D-ALLE or 3-hexadecyl-glyceryl ether for synthesis of L-ALLE.

Aufarbeitung

  1. temperaturerefluxed for 5 hours
  2. customwhile removing the water
  3. customformed by azeotropic distillation (compare W. J. Baumann and H. K. Mangold, J. Org. Chem. 29: 3055, 1964 and F. Paltauf, Monatsh. 99:1277, 1968)
  4. washThe resulting solution was washed with water (2×50 ml)
  5. customthe solvent was removed under reduced pressure
  6. additionA 100 ml mixture of 90:10:5 methanol:water:concentrated hydrochloric acid was added to the residue
  7. temperaturethe mixture was refluxed for 10 minutes
  8. extractionThe product was extracted with ether (200 ml)
  9. washwas washed consecutively with water (50 ml), 10% sodium hydroxide (20 ml) and again with water (volumes of 20 ml) until neutral
  10. customThe solvent was removed under reduced pressure
  11. customthe product (8.8 grams) was crystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-3854e28da7cb4f46b66a3f8b2214b572
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07186704B2

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