3-Hydroxybenzaldehyde → HCID 86742645, compound

Participants

Reaction Steps

A mixture of 2-chloromethyl quinoline hydrochloride (10 g, 47 mmol), 3-hydroxybenzaldehyde (6.3 g, 52 mmol), powdered potassium carbonate (14.5 g, 105 mmol), catalytic amounts of cesium carbonate (1.5 g) and sodium iodide (0.7 g) in dry acetone (150 ml) was refluxed for 14 hours. The solid residue was filtered off, and the filtrate was concentrated and dissolved in ethyl acetate. The organic solution was washed successively with 10% NaOH solution water and brine and then dried over MgSO4. All volatiles were removed to leave a yellowish solid weighing 14.8 g. This was recrystallized from hexanes-ethanol mixture to obtain 4-(3-(2-quinolinylmethoxy)phenyl-4-hydroxy-2-butanone as off-white crystals (11.8 g), mp 116°-9° C.

Provenance & Evidence