Water → 3,4-Diethylbenzophenone

HRID 583471

반응식

HRID 583471 반응식
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH3:10])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>C(Cl)Cl>[CH2:1]([C:3]1[CH:8]=[C:7]([CH:6]=[CH:5][C:4]=1[CH2:9][CH3:10])[C:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:22])[CH3:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 86571,2-DiethylbenzeneHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 215845983,4-Diethylbenzophenone수율 51.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred ice bath cooled solution of diethylbenzene (1.7 mL, 10 mmol) in methylene chloride (30 mL) under nitrogen was added aluminum chloride (2.93 g, 22 mmol). A slight exotherm resulted. To the resulting reaction mixture was added benzoyl chloride (1.2 mL, 10 mmol). The reaction mixture was allowed to warm to room temperature and was then stirred at room temperature for 1.5 hours. The reaction mixture was poured into 60 mL of iced water and stirred for 20 minutes. The resulting mixture was extracted with methylene chloride (2×40 mL). The combined extracts were dried over magnesium sulfate and concentrated in vacuo to afford the crude product as an orange oil. The crude product was purified by flash column chromatography (silica gel, 2.5% ethyl acetate/hexane) to afford 1.22 g (51%) of the product as a yellow oil: 1H NMR (CDCl3) δ 7.85-7.41 (m, 7H), 7.30-7.20 (m, 1H) 2.83-2.61 (m, 4H), 1.35-1.17 (m, 6H); 13C NMR (CDCl3) δ 196.8, 147.0, 141.9, 138.1, 135.3, 132.1, 132.1, 130.1, 130.0, 128.1, 128.1, 25.6, 25.4, 15.1, 15.0; Anal. Calcd for C17H18O. Theoretical: C, 85.67; H, 7.61. Found: C, 85.38; H, 7.42.

후처리

  1. customA slight exotherm resulted
  2. customTo the resulting reaction mixture
  3. stirringstirred for 20 minutes
  4. extractionThe resulting mixture was extracted with methylene chloride (2×40 mL)
  5. dry with materialThe combined extracts were dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto afford the crude product as an orange oil
  8. customThe crude product was purified by flash column chromatography (silica gel, 2.5% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-56bd2c972cc34b548f350f35ca3c6715
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05929117

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