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

HRID 2218902ノート

反応式

HRID 2218902 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6ce7fb14ca5848b6b219ecf3a7638dc9
出典データセット
uspto-grants-2008_08
特許番号
US07410971B2

反応ノート

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