4-Hydroxybenzaldehyde → 4-(2-quinolinylmethoxy)Benzaldehyde

Participants

Reaction Steps

To a solution of 4-hydroxybenzaldehyde (3.66 g, 30 mmol) and potassium carbonate (8.24 g, 60 mmol) in DMF (75 mL) was added 2-chloromethylquinoline hydrochloride (6.42 g, 30 mmol), and the resulting solution was stirred at ambient temperature for 16 hours. The reaction mixture was then poured into water (100 mL) and extracted with ethyl acetate (100 mL). The extract was dried over MgSO4 and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 2:1 hexane-ethyl acetate to afford 4-(2-quinolylmethoxy)benzaldehyde (5.8 g, 74%) as a crystalline compound.

Provenance & Evidence