Cumene → 4-Chloro-4'-isopropylbutyrophenone

HRID 413516

반응식

HRID 413516 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 987444-Chloro-4'-isopropylbutyrophenone수율 86.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

반응 조건

온도
6.5 °C

실험 절차

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% sodium bicarbonate (33×300 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.

후처리

  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% sodium bicarbonate (33×300 mL) and water (3×300 mL)
  5. dry with materialDry (MgSO4)
  6. filtrationfilter
  7. washwash with methylene chloride (150 mL)
  8. customEvaporate the solvent

출처 및 근거

ORD 기록
ord-8a5f566d56054027b32530f0941fed97
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06566526B2

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