反応 #49534

反応方程式

chloromethyl methyl ether

3-Chloro-4-hydroxybenzoic acid

potassium hydroxide

diisopropylethylamine

chloromethyl methyl ether

→

3-chloro-4-methoxymethoxybenzoic acid

収率 95.1%

溶媒

dichloromethane

methanol

反応条件

後処理

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
   その他The solvent was evaporated under reduced pressure
6. 6
   workup.ADDITIONthe residue was added with 4 mol/L hydrochloric acid and water
7. 7
   抽出by extracting with ethyl acetate
8. 8
   洗浄The organic layer was washed with saturated brine
9. 9
   乾燥dried over anhydrous sodium sulfate
10. 10
    その他The solvent was evaporated under reduced pressure

実験手順

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%).

出典