Methyl iodide → 1-Benzyl-2-methyl-3-(12cyclohexyldodecyl)glycerine

HRID 231269Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 231269
[H-].[Na+].[CH2:3]([O:10][CH2:11][CH:12]([CH2:14][O: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][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[OH:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:34]I>O1CCCC1>[CH2:3]([O:10][CH2:11][CH:12]([CH2:14][O: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][CH:28]1[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1)[O:13][CH3:34])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 539422351-Benzyl-3-(12-cyclohexyldodecyl)glycerine

Produkt 1

HCID 200348531-Benzyl-2-methyl-3-(12cyclohexyldodecyl)glycerine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

In 70 ml of tetrahydrofuran is suspended 0.86 g of sodium hydride, to which a solution of 10.2 g of 1-benzyl-3-(12-cyclohexyldodecyl)glycerine in 50 ml of tetrahydrofuran is added dropwise at room temperature with stirring. After 40 minutes stirring at room temperature, 5.11 g of methyl iodide is added and the mixture is further stirred for 2 hours. The solvent is then distilled off under reduced pressure and the residue is extracted with hexane. The extract layer is washed with water, dried and concentrated to obtain crude 1-benzyl-2-methyl-3-(12cyclohexyldodecyl)glycerine which in turn is dissolved in a mixed solvent consisting of 100 ml of ethanol and 30 ml of acetic acid. The solution is shaked in the presence of 10% palladium-carbon under hydrogen streams. The catalyst is removed by filtration and the filtrate is concentrated to obtain 9.6 g of the captioned compound as a crude product.

Aufarbeitung

  1. stirringAfter 40 minutes stirring at room temperature
  2. stirringthe mixture is further stirred for 2 hours
  3. distillationThe solvent is then distilled off under reduced pressure
  4. extractionthe residue is extracted with hexane
  5. washThe extract layer is washed with water
  6. customdried
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b6661016ef73458b8dd179734ef0b60f
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04845219

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