Water → HCID 54395130, Verbindung

HRID 384584

Reaktionsgleichung

Reaktionsgleichung von HRID 384584
[CH2:1]([CH:3]1[O:5][CH2:4]1)Cl.[OH-].[Na+].O.[OH:9][C:10]([CH3:24])([CH3:23])[C:11]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][OH:22])=[CH:15][CH:14]=1)=[O:12]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.COCCOC>[OH:9][C:10]([CH3:24])([CH3:23])[C:11]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][O:22][CH2:1][CH:3]2[CH2:4][O:5]2)=[CH:15][CH:14]=1)=[O:12]

Komponenten

7

Edukt 4

HCID 962WaterHCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 862662-Hydroxy-1-(4-(hydroxyethoxy)phenyl)-2-methyl-1-propanone

Produkt 1

HCID 54395130HCID 54395130, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

Epichlorohydrin (24 g, 0.261 mol) is added to a mixture of 16.31 g (0.408 mol) of sodium hydroxide, 45 ml of water, and 0.761 g (2.24 mmol) of tetrabutylammonium hydrogen sulfate that is previously cooled in an ice-water bath for 20 minutes. To this mixture is added dropwise over 45 minutes with rapid stirring, a solution of 10.32 g (46.0 mmol) of 2-hydroxy-1-[4-(2-hydroxy-ethoxy)phenyl]-2-methylpropan-1-one in 95 ml of 1,2-dimethoxyethane. The reaction mixture is stirred overnight at room temperature. The aqueous layer is removed, and the organic layer is concentrated. Purification by flash chromatography on silica gel (1:1 heptane:ethyl acetate) affords 9.20 g (71% of theoretical yield) of the title compound, a pale yellow liquid.

Aufarbeitung

  1. temperatureis previously cooled in an ice-water bath for 20 minutes
  2. additionTo this mixture is added dropwise over 45 minutes with rapid stirring
  3. customThe aqueous layer is removed
  4. concentrationthe organic layer is concentrated
  5. customPurification by flash chromatography on silica gel (1:1 heptane:ethyl acetate)
  6. customaffords

Quellen und Nachweise

ORD-Eintrag
ord-7c56b95367ff400fbe725bfb25a67097
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367743B2

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