Reacción #49534

Ecuación de reacción

chloromethyl methyl ether

3-Chloro-4-hydroxybenzoic acid

potassium hydroxide

diisopropylethylamine

chloromethyl methyl ether

→

3-chloro-4-methoxymethoxybenzoic acid

Rendimiento 95.1%

Disolventes

dichloromethane

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling
2. 2
   Temperaturacooling
3. 3
   workup.STIRRINGstirred at room temperature for 1.5 hours
4. 4
   workup.STIRRINGstirred at room temperature for 18 hours
5. 5
   OtroThe solvent was evaporated under reduced pressure
6. 6
   workup.ADDITIONthe residue was added with 4 mol/L hydrochloric acid and water
7. 7
   Extracciónby extracting with ethyl acetate
8. 8
   LavadoThe organic layer was washed with saturated brine
9. 9
   Secadodried over anhydrous sodium sulfate
10. 10
    OtroThe solvent was evaporated under reduced pressure

Procedimiento

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%).

Fuente