Cumene → 4-Chloro-4'-isopropylbutyrophenone

HRID 411890

反応式

HRID 411890 の反応式
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][CH2:6][CH2:7][CH2:8][C:9](Cl)=[O:10].[C:12]1([CH:18]([CH3:20])[CH3:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(Cl)Cl>[Cl:5][CH2:6][CH2:7][CH2:8][C:9]([C:15]1[CH:16]=[CH:17][C:12]([CH:18]([CH3:20])[CH3:19])=[CH:13][CH:14]=1)=[O:10]

参加物

5

反応物 3

HCID 7406CumeneHCID 783704-Chlorobutyryl chlorideHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 987444-Chloro-4'-isopropylbutyrophenone収率 86.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

反応条件

温度
6.5 °C

実験手順

Slurry aluminum chloride (140.9 g, 1.075 mol) and 4-chlorobutyryl chloride (148 g, 1.05 mol) in methylene chloride (1.0L) add, by dropwise addition, cumene (125 g, 1.04 mol) over a thirty minute period under a nitrogen atmosphere while maintaining the internal temperature between 5-8° C. with an ice bath. Allow the stirred solution to come to room temperature and continue stirring under nitrogen for 14 hours. Cautiously add the methylene chloride solution to 1L of crushed ice with stirring and add additional methylene chloride (400 mL). Separate the organic phase and wash with 10% hydrochloric acid (3×300 mL), water (3×300 mL), 10% solution bicarbonate (3×300 mL) and water (3×300 mL). Dry (MgSO4), filter and wash with methylene chloride (150 mL). Evaporate the solvent to give the title compound (203 g, 86%) as a clear oil which crystallizes on standing; mp 35-37° C.

後処理

  1. customto come to room temperature
  2. stirringwith stirring
  3. customSeparate the organic phase
  4. washwash with 10% hydrochloric acid (3×300 mL), water (3×300 mL), 10% solution bicarbonate (3×300 mL) and water (3×300 mL)
  5. dry with materialDry (MgSO4)
  6. filtrationfilter
  7. washwash with methylene chloride (150 mL)
  8. customEvaporate the solvent

出典と根拠

ORDレコード
ord-1318968197cc4335bdf9dda3ae9c7044
出典データセット
uspto-grants-2003_05
特許番号
US06559312B2

関連ノート

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