Sodium Iodide → Benzaldehyde, 3,5-dimethoxy-4-(phenylmethoxy)-

Participants

Reaction Steps

A mixture of syringaldehyde (3.64 g, 20 mmol), benzyl chloride (2.52 g 20 mmol), NaI (2 g) and potassium carbonate (2.76 g, 20 mmol) in anhydrous acetone (60 mL) were refluxed for 5 h and cooled to room temperature. The solid materials were removed by filtration, the filtrate was concentrated and the residue was purified by chromatography on silica gel (230-400 mesh, 50 g) using 5% EtOAc in hexane as the eluent to obtain 13j (4.3 g, 79%); mp 62°-63° C.

Provenance & Evidence