4-Hydroxybenzaldehyde → HCID 23078883, compound

Participants

Reaction Steps

To a solution of 4-hydroxybenzaldehyde (2.44 g) in N,N-dimethylformamide (20 mL) were added cesium carbonate (7.17 g), benzyl 3-bromopropyl ether (4.81 g) and a catalytic amount of sodium iodide, and the mixture was stirred at room temperature for 4 days. The reaction mixture was poured into water, and the resulting mixture was extracted with diethyl ether. The organic layer was washed with water, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give 4-(3-benzyloxypropoxy)benzaldehyde. This material was dissolved in ethanol (20 mL). To the solution was added sodium borohydride (757 mg), and the mixture was stirred at room temperature for 3 hours. To the reaction mixture was added methanol, and the resulting mixture was concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with diethyl ether. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=5/1-2/1) to give the title compound (5.17 g).

Provenance & Evidence