反应 #49551

反应方程式

3-hydroxy-4-methylbenzoic acid

diisopropylethylamine

chloromethyl methyl ether

→

3-methoxymethoxy-4-methylbenzoic acid

收率 104.7%

溶剂

dichloromethane

反应条件

后处理

1. 1
   其他The 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
   其他The solvent was evaporated under reduced pressure
5. 5
   workup.ADDITIONThe residue was added with 4 mol/L hydrochloric acid
6. 6
   萃取extracted with ethyl acetate
7. 7
   洗涤The organic layer was washed with saturated brine
8. 8
   干燥dried over anhydrous sodium sulfate
9. 9
   其他The solvent was evaporated under reduced pressure

实验过程

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).

来源