Reaction #1833270

Reaction equation

2-Methoxyethoxymethyl chloride

4-hydroxybenzaldehyde

K2CO3

→

4-((2-methoxyethoxy)methoxy)benzaldehyde

Yield 80.0%

Solvents

acetone

Conditions

Workup

1. 1
   Otherto reach room temperature
2. 2
   OtherAfter removal of the solvent
3. 3
   workup.DISSOLUTIONthe crude residue was dissolved in EtOAc (50 mL)
4. 4
   Washconsecutively washed with water (50 mL) and NaOH (10% aqueous solution, 2×20 mL)
5. 5
   DryingThe organic layer was dried over anhydrous Na2SO4
6. 6
   Filtrationfiltered
7. 7
   OtherAfter removal of the solvent

Procedure

2-Methoxyethoxymethyl chloride (5.10 mL, 45.0 mmol) was slowly added to a mixture of 4-hydroxybenzaldehyde (5.00 g, 40.9 mmol) and K2CO3 (6.20 g, 45.0 mmol) in acetone (70 mL) cooled at 0° C. The mixture was allowed to reach room temperature and stirred for 40 h. After removal of the solvent, the crude residue was dissolved in EtOAc (50 mL) and consecutively washed with water (50 mL) and NaOH (10% aqueous solution, 2×20 mL). The organic layer was dried over anhydrous Na2SO4 and filtered. After removal of the solvent, 6.85 g of 4-((2-methoxyethoxy)methoxy)benzaldehyde were obtained [Rf=0.6 (50% AcOEt/Hexanes), colorless oil, 80% yield], that were used without further purification.

Source