تفاعل #49551

معادلة التفاعل

3-hydroxy-4-methylbenzoic acid

diisopropylethylamine

chloromethyl methyl ether

→

3-methoxymethoxy-4-methylbenzoic acid

المردود 104.7%

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر