4-Methoxyphenol → 1-((2-Ethylhexyl)oxy)-4-methoxybenzene

HRID 21884

反応式

HRID 21884 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.Br[CH2:11][CH:12]([CH2:17][CH3:18])[CH2:13][CH2:14][CH2:15][CH3:16]>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:11][CH:12]([CH2:17][CH3:18])[CH2:13][CH2:14][CH2:15][CH3:16])=[CH:5][CH:4]=1

参加物

4

反応物 2

HCID 90154-MethoxyphenolHCID 868042-Ethylhexyl bromide

生成物 1

HCID 33410051-((2-Ethylhexyl)oxy)-4-methoxybenzene収率 43.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

Sodium metal (6.50 g, 283 mmol) was dissolved in dry methanol (100 ml) under Ar to give a 2.5M solution of sodium methoxide. A solution of 4-methoxyphenol (29.3 g, 236 mmol) in dry methanol (150 ml) was added and this mixture was heated to reflux for 30 min. After cooling to room temperature, a solution of 1-bromo-2-ethylhexane (46.5 g, 259 mmol) in dry methanol (150 ml) was added dropwise. The mixture was then heated to reflux for 18 hours. The solvent was removed in vacuo, the residue dissolved in ether (200 ml), washed with dilute aqueous sodium hydroxide (500 ml ) and water (500 ml ), dried over MgSO4 and concentrated in vacuo again. Distillation at 120° C./0.1 mm Hg afforded 24.2 g (43%) 1-methoxy-4-(2'-ethylhexyloxy)benzene.

後処理

  1. temperaturethis mixture was heated
  2. temperatureto reflux for 30 min
  3. temperatureThe mixture was then heated
  4. temperatureto reflux for 18 hours
  5. customThe solvent was removed in vacuo
  6. dissolutionthe residue dissolved in ether (200 ml)
  7. washwashed with dilute aqueous sodium hydroxide (500 ml ) and water (500 ml )
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo again
  10. distillationDistillation at 120° C./0.1 mm Hg

出典と根拠

ORDレコード
ord-2f9bf7f3038b4bf7aa5a7d6f8c8af502
出典データセット
uspto-grants-1995_06
特許番号
US05425125

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