Réaction #51933

Équation de réaction

3-hydroxybenzaldehyde

potassium carbonate

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

→

title compound

Rendement 19.6%

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

Rendement 19.6%

Solvants

acetone

Conditions de réaction

Traitement

1. 1
   Températurerefluxed under nitrogen for 18 h
2. 2
   Températurecooled
3. 3
   Filtrationfiltered
4. 4
   ConcentrationThe filtrate is concentrated under reduced pressure
5. 5
   Autrethe residue partitioned between CH2Cl2 and 1N NaOH
6. 6
   ExtractionThe aqueous phase is extracted with two additional portions of CH2Cl2
7. 7
   Séchagethe combined organic extracts dried (MgSO4)
8. 8
   Concentrationconcentrated under reduced pressure

Mode opératoire

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.

Source