Water → N-[4-[[(E)-3-(4-Isopropylphenyl)-2-propenyl]oxy]-2,3,6-trimethylphenyl]formamide

HRID 2211742Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2211742
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH:9][CH:10]=[O:11])=[C:4]([CH3:12])[C:3]=1[CH3:13].[H-].[Na+].Br[CH2:17]/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][C:23]([CH:26]([CH3:28])[CH3:27])=[CH:22][CH:21]=1.O>CN(C)C=O>[CH:26]([C:23]1[CH:22]=[CH:21][C:20](/[CH:19]=[CH:18]/[CH2:17][O:1][C:2]2[CH:7]=[C:6]([CH3:8])[C:5]([NH:9][CH:10]=[O:11])=[C:4]([CH3:12])[C:3]=2[CH3:13])=[CH:25][CH:24]=1)([CH3:28])[CH3:27]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 21961295N-(4-hydroxy-2,3,6-trimethylphenyl)formamideHCID 219613131-[(E)-3-bromo-1-propenyl]-4-isopropylbenzene

Produkt 1

HCID 21961342N-[4-[[(E)-3-(4-Isopropylphenyl)-2-propenyl]oxy]-2,3,6-trimethylphenyl]formamideAusbeute 59,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of N-(4-hydroxy-2,3,6-trimethylphenyl)formamide (5.20 g, 29.0 mmol) in N,N-dimethylformamide (30 ml) was added at 0° C. under a nitrogen atmosphere sodium hydride (a 60% dispersion in liquid paraffin, 1.39 g, 34.8 mmol) and the resulting mixture was stirred at the same temperature for 10 minutes. To the reaction solution was added 1-[(E)-3-bromo-1-propenyl]-4-isopropylbenzene (9.00 g, 37.7 mmol) and the resulting mixture was stirred at room temperature for 30 minutes. Water was added into the reaction solution and the product was extracted twice with ethyl acetate. The combined extracts were washed with water, dried on magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was crystallized from ethyl acetate-hexane to obtain 5.80 g (59% yield) of the title compound. Melting point: 165-167° C.

Aufarbeitung

  1. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  2. extractionthe product was extracted twice with ethyl acetate
  3. washThe combined extracts were washed with water
  4. customdried on magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was crystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-ef768ddfeb8d47bfb0c9e57e5709577e
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07101867B2

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