반응 #49551

반응 방정식

3-hydroxy-4-methylbenzoic acid

diisopropylethylamine

chloromethyl methyl ether

→

3-methoxymethoxy-4-methylbenzoic acid

수율 104.7%

용매

dichloromethane

반응 조건

후처리

1. 1
   기타The 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
   기타The solvent was evaporated under reduced pressure
5. 5
   workup.ADDITIONThe residue was added with 4 mol/L hydrochloric acid
6. 6
   추출extracted with ethyl acetate
7. 7
   세척The organic layer was washed with saturated brine
8. 8
   건조dried over anhydrous sodium sulfate
9. 9
   기타The solvent was evaporated under reduced pressure

실험 절차

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).

출처