Reaktion #49528

Reaktionsgleichung

4-Formyl-3-hydroxybenzoic acid

diisopropylethylamine

chloromethyl methyl ether

→

4-formyl-3-methoxymethoxybenzoic acid

Ausbeute 80.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   SonstigeThe solvent was evaporated under reduced pressure
3. 3
   workup.DISSOLUTIONthe residue was dissolved in methanol (40 mL)
4. 4
   workup.ADDITIONthe solution was added with 2 mol/L aqueous potassium hydroxide solution (40 mL)
5. 5
   workup.STIRRINGstirred at room temperature for 1 hour
6. 6
   SonstigeMethanol was evaporated under reduced pressure
7. 7
   workup.ADDITIONthe residue was added with 4 mol/L hydrochloric acid and water
8. 8
   FiltrationThe precipitated solid was collected by filtration
9. 9
   Waschenwashed with water
10. 10
    Sonstigeby drying under reduced pressure

Vorschrift

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%).

Quelle