反应 #49534

反应方程式

chloromethyl methyl ether

3-Chloro-4-hydroxybenzoic acid

potassium hydroxide

diisopropylethylamine

chloromethyl methyl ether

→

3-chloro-4-methoxymethoxybenzoic acid

收率 95.1%

溶剂

dichloromethane

methanol

反应条件

后处理

1. 1
   温度cooling
2. 2
   温度cooling
3. 3
   workup.STIRRINGstirred at room temperature for 1.5 hours
4. 4
   workup.STIRRINGstirred at room temperature for 18 hours
5. 5
   其他The solvent was evaporated under reduced pressure
6. 6
   workup.ADDITIONthe residue was added with 4 mol/L hydrochloric acid and water
7. 7
   萃取by extracting with ethyl acetate
8. 8
   洗涤The organic layer was washed with saturated brine
9. 9
   干燥dried over anhydrous sodium sulfate
10. 10
    其他The solvent was evaporated under reduced pressure

实验过程

3-Chloro-4-hydroxybenzoic acid 0.5 hydrate (2.00 g, 11.6 mmol) was suspended in dichloromethane (50 mL), and the suspension was added with diisopropylethylamine (8.10 mL, 46.5 mmol) and chloromethyl methyl ether (1.80 mL, 23.7 mmol), under ice-cooling. The reaction mixture was warmed to room temperature and stirred for 1.5 hours. The reaction mixture was added with chloromethyl methyl ether (0.45 mL, 5.92 mmol) under ice-cooling, and stirred at room temperature for 1.5 hours. The reaction mixture was added with methanol (100 mL) and 4 mol/L aqueous potassium hydroxide solution (50 mL) and stirred at room temperature for 18 hours. The solvent was evaporated under reduced pressure, and the residue was added with 4 mol/L hydrochloric acid and water, followed by extracting with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain 3-chloro-4-methoxymethoxybenzoic acid (2.39 g, yield 95%).

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