反応 #49545

反応方程式

isovanillic acid

diisopropylethylamine

chloromethyl methyl ether

→

3-methoxymethoxy-4-methoxybenzoic acid

収率 76.5%

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.ADDITIONtreated with 4 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
   ろ過The precipitated solid was collected by filtration
7. 7
   洗浄washed with water
8. 8
   その他by drying under reduced pressure

実験手順

In a similar manner to Step 1 of Example 347, isovanillic acid (5.00 g, 29.7 mmol) was suspended in dichloromethane (100 mL), and the suspension was treated with diisopropylethylamine (22.8 mL, 131 mmol) and chloromethyl methyl ether (4.96 mL, 65.4 mmol). The solvent was evaporated under reduced pressure. The residue was dissolved in methanol (50 mL) and treated with 4 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. The precipitated solid was collected by filtration and washed with water, followed by drying under reduced pressure to obtain 3-methoxymethoxy-4-methoxybenzoic acid (4.82 g, yield 76%).

出典