反応 #49551

反応方程式

3-hydroxy-4-methylbenzoic acid

diisopropylethylamine

chloromethyl methyl ether

→

3-methoxymethoxy-4-methylbenzoic acid

収率 104.7%

溶媒

dichloromethane

反応条件

後処理

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

実験手順

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).

出典