Reacción #49551

Ecuación de reacción

3-hydroxy-4-methylbenzoic acid

diisopropylethylamine

chloromethyl methyl ether

→

3-methoxymethoxy-4-methylbenzoic acid

Rendimiento 104.7%

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.ADDITIONthe solution was treated with 2 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
   Extracciónextracted with ethyl acetate
7. 7
   LavadoThe organic layer was washed with saturated brine
8. 8
   Secadodried over anhydrous sodium sulfate
9. 9
   OtroThe solvent was evaporated under reduced pressure

Procedimiento

In a similar manner to Step 1 of Example 347, 3-hydroxy-4-methylbenzoic acid (2.00 g, 13.1 mmol) was suspended in dichloromethane (50 mL), and the suspension was treated with diisopropylethylamine (13.7 mL, 78.6 mmol) and chloromethyl methyl ether (5.00 mL, 65.8 mmol). The solvent was evaporated under reduced pressure. The residue was dissolved in methanol (50 mL), and the solution was treated with 2 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 and extracted 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-methoxymethoxy-4-methylbenzoic acid (2.69 g).

Fuente