Dimethylformamide → Benzene, 1,2,5-trimethyl-3-[(2-methyl-2-propenyl)oxy]-

HRID 2063777Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2063777
Br[CH2:2][C:3]([CH3:5])=[CH2:4].CN(C=O)C.[CH3:11][C:12]1[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=1[OH:20].C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C>[CH3:18][C:17]1[CH:16]=[C:15]([CH3:19])[CH:14]=[C:13]([O:20][CH2:4][C:3]([CH3:5])=[CH2:2])[C:12]=1[CH3:11]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 127692,3,5-TrimethylphenolHCID 3577853-Bromo-2-methyl-1-propene

Produkt 1

HCID 11830229Benzene, 1,2,5-trimethyl-3-[(2-methyl-2-propenyl)oxy]-Ausbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

3-bromo-2-methylpropene (29.8 g, 221 mmol) was added to a mixture of DMF (130 mL) containing 2,3,5-trimethylphenol (25.0 g, 184 mmol) and potassium carbonate (50.9 g, 368 mmol), and the resulting mixture was stirred at 80° C. for 15 hours. After cooled to room temperature, the reaction solution was distributed using ethyl acetate and water. The organic layer was washed with saturated saline, and then dried using anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 50:1 to 9:1) to give 33.6 g of the title compound (yield: 96%) as an oily product.

Aufarbeitung

  1. temperatureAfter cooled to room temperature
  2. washThe organic layer was washed with saturated saline
  3. customdried
  4. customThe solvent was removed under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 50:1 to 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-0b0af8442c0343858f8e3e677e48c7cf
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288390B2

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