反応 #11745

反応方程式

4-chloro-2-chloromethyl-1-methoxy-benzene

potassium cyanide

18-crown-6

→

title compound

収率 98.2%

(5-Chloro-2-methoxy-phenyl)-acetonitrile

収率 98.2%

溶媒

acetonitrile

ethyl acetate

反応条件

後処理

1. 1
   洗浄washed with aqueous sodium hydrogen carbonate
2. 2
   乾燥The organic layer was dried over magnesium sulfate
3. 3
   濃縮concentrated in vacuo
4. 4
   その他The crude product was purified
5. 5
   洗浄eluting with methylene chloride

実験手順

To a solution of (5-chloro-2-methoxy-phenyl)-methanol (17.1 g, 99.1 mmol) in methylene chloride (100 mL) was added thionyl chloride (14.5 mL, 198 mmol). The reaction was stirred at reflux for 3 hours, cooled to room temperature and concentrated in vacuo. The crude product was dissolved in methylene chloride and washed with saturated aqueous sodium hydrogen carbonate then dried over magnesium sulfate. Concentration in vacuo gave 4-chloro-2-chloromethyl-1-methoxy-benzene (18.4 g). To a solution of 4-chloro-2-chloromethyl-1-methoxy-benzene (18.4 g, 96.4 mmol) in acetonitrile (100 mL) was added potassium cyanide (12.5 g, 193 mmol) and 18-crown-6 (2.54 g, 9.64 mmol). The reaction was stirred 12 hours at ambient temperature, diluted with ethyl acetate and washed with aqueous sodium hydrogen carbonate. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by passing it through a pad of silica gel, eluting with methylene chloride to give the title compound (17.2 g).

出典