3-Hydroxybenzaldehyde → Methyl 4-((3-formylphenoxy)methyl)benzoate

Participants

Reaction Steps

A slurry of methyl 4-(bromomethyl)benzoate (1.4 g, 6.14 mmol), K2CO3 (1.02 g, 7.37 mmol), 3-hydroxybenzaldehyde (899 mg, 7.37 mmol) in acetone (20 mL) was stirred at room temperature for 16 hours. The solids were filtered, the filtrate partitioned between EtOAc (50 mL) and water (20 mL). The layers were separated and the aqueous phase back-extracted with EtOAc (3×30 mL) The combined organic phases were washed with brine (30 mL) and dried over MgSO4. The solvent was removed in vacuo and the residue was purified via silica gel chromatography (eluting with 0-20% isohexane/EtOAc) to give the title compound (464 mg, 28% yield) as a white solid.

Provenance & Evidence