Реакция #51933

Уравнение реакции

3-hydroxybenzaldehyde

potassium carbonate

1-bromo-2-(2-methoxyethoxy)ethane

→

title compound

Выход 19.6%

3-[2-(2-Methoxyethoxy)ethoxy]benzaldehyde

Выход 19.6%

Растворители

acetone

Условия реакции

Обработка

1. 1
   Температураrefluxed under nitrogen for 18 h
2. 2
   Температураcooled
3. 3
   Фильтрацияfiltered
4. 4
   КонцентрированиеThe filtrate is concentrated under reduced pressure
5. 5
   Другоеthe residue partitioned between CH2Cl2 and 1N NaOH
6. 6
   ЭкстракцияThe aqueous phase is extracted with two additional portions of CH2Cl2
7. 7
   Сушкаthe combined organic extracts dried (MgSO4)
8. 8
   Концентрированиеconcentrated under reduced pressure

Методика

A mixture of 3.66 g of 3-hydroxybenzaldehyde, 4.6 g of powdered potassium carbonate, and 5.5 g of 1-bromo-2-(2-methoxyethoxy)ethane in 40 ml of acetone is stirred and refluxed under nitrogen for 18 h, then cooled and filtered. The filtrate is concentrated under reduced pressure, and the residue partitioned between CH2Cl2 and 1N NaOH. The aqueous phase is extracted with two additional portions of CH2Cl2, and the combined organic extracts dried (MgSO4) and concentrated under reduced pressure. Flash chromatography of the residue on silica using 20% EtOAc in CH2Cl2 affords 1.32 g of the title compound as a pale yellow oil.

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