Hydrogen Bromide → 4-Methyl-2-(3,3,5,5-tetramethylcyclohexyl)phenol

HRID 32258Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 32258
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[CH:10]1[CH2:15][C:14]([CH3:17])([CH3:16])[CH2:13][C:12]([CH3:19])([CH3:18])[CH2:11]1.Br.C(=O)([O-])O.[Na+].C(OCC)(=O)C>C(O)(=O)C>[CH3:9][C:6]1[CH:7]=[CH:8][C:3]([OH:2])=[C:4]([CH:10]2[CH2:15][C:14]([CH3:17])([CH3:16])[CH2:13][C:12]([CH3:19])([CH3:18])[CH2:11]2)[CH:5]=1

Komponenten

6

Edukt 4

HCID 260Hydrogen BromideHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 231424201-Methoxy-4-methyl-2-(3,3,5,5-tetramethylcyclohexyl)benzene

Produkt 1

HCID 231428954-Methyl-2-(3,3,5,5-tetramethylcyclohexyl)phenolAusbeute 47,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 1-methoxy-4-methyl-2-(3,3,5,5-tetramethylcyclohexyl)benzene (1.0 g, 3.84 mmol) produced in Example (104b) in acetic acid (5 mL) was added 48% hydrobromic acid (10 mL, 59.3 mmol), followed by reflux for 12 hours. Saturated aqueous solution of sodium hydrogencarbonate was added to the cooled reaction mixture, and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and the filtrate was concentrated under reduced pressure to give a residue, which was purified by silica gel column chromatography (ethyl acetate/heptane) to give 450 mg of the title compound as a light yellow oil.

Aufarbeitung

  1. temperatureby reflux for 12 hours
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto give a residue, which
  5. customwas purified by silica gel column chromatography (ethyl acetate/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-788786ab72244ce09bc41176047c94c2
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425554B2

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