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

HRID 1787123Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1787123
[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][C:18]([CH3:29])=[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=O)C>[CH:26]([C:23]1[CH:22]=[CH:21][C:20]([CH:19]=[C:18]([CH3:29])[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 687079861-(3-Bromo-2-methyl-1-propenyl)-4-isopropylbenzene

Produkt 1

HCID 73856746N-(4-((3-(4-Isopropylphenyl)-2-methyl-2-propenyl)oxy)-2,3,6-trimethylphenyl)formamideAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of N-(4-hydroxy-2,3,6-trimethylphenyl)formamide (3.00 g, 16.7 mmol) in DMF (30 mL) was added sodium hydride (a 60% liquid paraffin dispersion, 0.74 g, 18.4 mmol) under nitrogen atmosphere at 0° C., and the mixture was stirred at the same temperature for 10 minutes. To the reaction solution was added 1-(3-bromo-2-methyl-1-propenyl)-4-isopropylbenzene synthesized in Reference Example 108 (4.66 g, 18.4 mmol) and the mixture was stirred at room temperature for 30 minutes. Water was added to the reaction solution and the product was twice extracted with ethyl acetate. The combined extract was washed with water, dried over magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was crystallized from ethyl acetate-hexane to obtain 3.70 g (yield 63%) of the title compound. Melting point: 153-155° C.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. extractionthe product was twice extracted with ethyl acetate
  3. extractionThe combined extract
  4. washwas washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was crystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-fc93ca00e0ac440ea16e69be383eabfa
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07507841B2

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