Реакция #49545

Уравнение реакции

isovanillic acid

diisopropylethylamine

chloromethyl methyl ether

→

3-methoxymethoxy-4-methoxybenzoic acid

Выход 76.5%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   ДругоеThe 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
   ДругоеThe solvent was evaporated under reduced pressure
5. 5
   workup.ADDITIONThe residue was added with 4 mol/L hydrochloric acid
6. 6
   ФильтрацияThe precipitated solid was collected by filtration
7. 7
   Промывкаwashed with water
8. 8
   Другоеby drying under reduced pressure

Методика

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%).

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