Ethyl Bromide → 2-tert-Butyl-4-ethoxyphenol

HRID 1457598

Reaktionsgleichung

Reaktionsgleichung von HRID 1457598
[C:1]([C:5]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:6]=1[OH:7])([CH3:4])([CH3:3])[CH3:2].[CH2:13](Br)[CH3:14].[H-].[Na+]>CN(C)C=O>[CH2:13]([O:12][C:10]1[CH:9]=[CH:8][C:6]([OH:7])=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:11]=1)[CH3:14]

Komponenten

5

Edukt 3

HCID 6332Ethyl BromideHCID 16043Tert-ButylhydroquinoneHCID 24758Sodium hydride

Produkt 1

HCID 124236482-tert-Butyl-4-ethoxyphenolAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A mixture of 19.85 g of tert-butylhydroquinone, 10.7 ml of ethyl bromide and 200 ml of dimethylformamide (DMF) was cooled to -78° C., and 4.82 g of 62.5% sodium hydride was added to the mixture. The temperature of the mixture was raised to 0° C., and the mixture was further stirred under ice-cooling for 30 minutes. The reaction mixture was poured into ice water, and the mixture was extracted with ethyl acetate. The extract was washed and dried, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=10:1), and recrystallized from hexane to give 5.045 g of 4-ethoxy-2-tert-butylphenol (yield: 22%, melting point: 96°-98° C.).

Aufarbeitung

  1. temperatureThe temperature of the mixture was raised to 0° C.
  2. temperaturecooling for 30 minutes
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed
  5. customdried
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=10:1)
  8. customrecrystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-0fcf3e76e20648fda250e06bb1d928a5
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05849732

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