Reacción #49545

Ecuación de reacción

isovanillic acid

diisopropylethylamine

chloromethyl methyl ether

→

3-methoxymethoxy-4-methoxybenzoic acid

Rendimiento 76.5%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvent was evaporated under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in methanol (50 mL)
3. 3
   workup.ADDITIONtreated with 4 mol/L aqueous potassium hydroxide solution (50 mL)
4. 4
   OtroThe solvent was evaporated under reduced pressure
5. 5
   workup.ADDITIONThe residue was added with 4 mol/L hydrochloric acid
6. 6
   FiltraciónThe precipitated solid was collected by filtration
7. 7
   Lavadowashed with water
8. 8
   Otroby drying under reduced pressure

Procedimiento

In a similar manner to Step 1 of Example 347, isovanillic acid (5.00 g, 29.7 mmol) was suspended in dichloromethane (100 mL), and the suspension was treated with diisopropylethylamine (22.8 mL, 131 mmol) and chloromethyl methyl ether (4.96 mL, 65.4 mmol). The solvent was evaporated under reduced pressure. The residue was dissolved in methanol (50 mL) and treated with 4 mol/L aqueous potassium hydroxide solution (50 mL). The solvent was evaporated under reduced pressure. The residue was added with 4 mol/L hydrochloric acid. The precipitated solid was collected by filtration and washed with water, followed by drying under reduced pressure to obtain 3-methoxymethoxy-4-methoxybenzoic acid (4.82 g, yield 76%).

Fuente