Allyl bromide → 4-Acetoxy-3,5-di-tert-butyl-1-(2-propenyloxy)benzene

HRID 1376974ノート

反応式

HRID 1376974 の反応式
[C:1]([O:4][C:5]1[C:10]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:9][C:8]([OH:15])=[CH:7][C:6]=1[C:16]([CH3:19])([CH3:18])[CH3:17])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][CH:28]=[CH2:29]>CC(C)=O>[C:1]([O:4][C:5]1[C:10]([C:11]([CH3:12])([CH3:14])[CH3:13])=[CH:9][C:8]([O:15][CH2:29][CH:28]=[CH2:27])=[CH:7][C:6]=1[C:16]([CH3:19])([CH3:18])[CH3:17])(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 111399982,6-DI-Tert-butyl-4-hydroxyphenyl acetate

生成物 1

HCID 110880374-Acetoxy-3,5-di-tert-butyl-1-(2-propenyloxy)benzene

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

4-Acetoxy-3,5-di-tert-butylphenol (10 g) and potassium carbonate (15.6 g) were dissolved in acetone (300 ml). After addition of 3-bromo-1-propene (6.55 ml), the mixture was refluxed for 24 h. The reaction mixture was concentrated under reduced pressure and water was added to the concentrate. The mixture was subjected to extraction with diethyl ether and the organic layer was washed with water and saturated brine, then dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane) to afford 4-acetoxy-3,5-di-tert-butyl-1-(2-propenyloxy)benzene (11 g) as a colorless liquid in a quantitative yield.

後処理

  1. temperaturethe mixture was refluxed for 24 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure and water
  3. additionwas added to the concentrate
  4. extractionThe mixture was subjected to extraction with diethyl ether
  5. washthe organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane)

出典と根拠

ORDレコード
ord-92915a9a68214567ae98903390062a93
出典データセット
uspto-grants-1997_09
特許番号
US05663373

反応ノート

読み込み中…