4-Hydroxybenzaldehyde → Benzaldehyde, 4-[(2-methoxyethoxy)methoxy]-

Temperature

0 °C

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.

1. customto reach room temperature
2. customAfter removal of the solvent
3. dissolutionthe crude residue was dissolved in EtOAc (50 mL)
4. washconsecutively washed with water (50 mL) and NaOH (10% aqueous solution, 2×20 mL)
5. dry with materialThe organic layer was dried over anhydrous Na2SO4
6. filtrationfiltered
7. customAfter removal of the solvent

ORD record

ord-37b6b627653040a8bd705c7a67c91b7b

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08859555B2