Chloromethyl Methyl Ether → 3-Chloro-4-methoxymethoxybenzoic acid

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%).

1. temperaturecooling
2. temperaturecooling
3. stirringstirred at room temperature for 1.5 hours
4. stirringstirred at room temperature for 18 hours
5. customThe solvent was evaporated under reduced pressure
6. additionthe residue was added with 4 mol/L hydrochloric acid and water
7. extractionby extracting with ethyl acetate
8. washThe organic layer was washed with saturated brine
9. dry with materialdried over anhydrous sodium sulfate
10. customThe solvent was evaporated under reduced pressure

ORD-Eintrag

ord-98ca684b2d7041bc8d3afabb280632b7

Quelldatensatz

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07745641B2