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

4-Formyl-3-hydroxybenzoic acid (2.20 g, 13.2 mmol) was suspended in dichloromethane (40 mL), and the suspension was added with diisopropylethylamine (9.20 mL, 52.8 mmol) and chloromethyl methyl ether (2.01 mL, 26.5 mmol) under ice-cooling. Then, the reaction mixture was warmed to room temperature and stirred for 1 hour. The solvent was evaporated under reduced pressure and the residue was dissolved in methanol (40 mL), and the solution was added with 2 mol/L aqueous potassium hydroxide solution (40 mL), and stirred at room temperature for 1 hour. Methanol was evaporated under reduced pressure and the residue was added with 4 mol/L hydrochloric acid and water. The precipitated solid was collected by filtration and washed with water, followed by drying under reduced pressure to obtain 4-formyl-3-methoxymethoxybenzoic acid (2.21 g, yield 80%).

1. temperaturecooling
2. customThe solvent was evaporated under reduced pressure
3. dissolutionthe residue was dissolved in methanol (40 mL)
4. additionthe solution was added with 2 mol/L aqueous potassium hydroxide solution (40 mL)
5. stirringstirred at room temperature for 1 hour
6. customMethanol was evaporated under reduced pressure
7. additionthe residue was added with 4 mol/L hydrochloric acid and water
8. filtrationThe precipitated solid was collected by filtration
9. washwashed with water
10. customby drying under reduced pressure

ORD-Eintrag

ord-8c84d9f0f0474201bd3b468686c19dd9

Quelldatensatz

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07745641B2