2,4-Dihydroxybenzaldehyde → 4-Benzyloxy-2-hydroxybenzaldehyde

To a 250 mL RB flask fitted with magnetic stirrer was charged with 30 mL of acetonitrile. To the stirred solvent were added 2,4-dihydroxybenzaldehyde (8.0 g, 57.0 mmol), potassium carbonate (15.77 g, 114.0 mmol). The reaction mixture was brought to 0° C., was added benzyl bromide (9.905 g, 57.0 mmol) in acetonitrile (100 mL) drop wise and stirred at room temperature for 3 h. The reaction mixture was concentrated to distill off the solvent. The residue was extracted with ethyl acetate (80 mL). The organic layer was washed with water (50 mL) and saturated brine solution (50 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The product obtained as a white solid (4.0 g, yield: 30.77%).

1. customTo a 250 mL RB flask fitted with magnetic stirrer
2. customwas brought to 0° C.
3. concentrationThe reaction mixture was concentrated
4. distillationto distill off the solvent
5. extractionThe residue was extracted with ethyl acetate (80 mL)
6. washThe organic layer was washed with water (50 mL) and saturated brine solution (50 mL)
7. dry with materialThe organic layer was dried over anhydrous Na2SO4
8. customthe solvent was removed under reduced pressure

ORD record

ord-ba29f467c568499db4367ac8eec721af

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09278915B2