反応 #453811

反応方程式

water

aluminum chloride

diethylbenzene

benzoyl chloride

→

product

収率 51.2%

3,4-Diethylbenzophenone

収率 51.2%

溶媒

methylene chloride

反応条件

後処理

1. 1
   その他A slight exotherm resulted
2. 2
   その他To the resulting reaction mixture
3. 3
   workup.STIRRINGstirred for 20 minutes
4. 4
   抽出The resulting mixture was extracted with methylene chloride (2×40 mL)
5. 5
   乾燥The combined extracts were dried over magnesium sulfate
6. 6
   濃縮concentrated in vacuo
7. 7
   その他to afford the crude product as an orange oil
8. 8
   その他The crude product was purified by flash column chromatography (silica gel, 2.5% ethyl acetate/hexane)

実験手順

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, 7 H), 7.30-7.20 (m, 1 H) 2.83-2.61 (m, 4 H), 1.35-1.17 (m, 6 H); 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.

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