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

HRID 32258Notes

Reaction equation

HRID 32258 reaction equation
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

Participants

6

Reactant 4

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

Product 1

HCID 231428954-Methyl-2-(3,3,5,5-tetramethylcyclohexyl)phenolYield 47.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-788786ab72244ce09bc41176047c94c2
Source dataset
uspto-grants-2008_09
Patent number
US07425554B2

Reaction notes

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