Vanillin → 4-Formyl-2-methoxyphenyl trifluoromethanesulfonate

Participants

Reaction Steps

To a mixture of 4-hydroxy-3-methoxybenzaldehyde (10.0 g, 65.7 mmol) and Et3N (13.0 g, 128.7 mmol) in anhydrous DCM (100 mL) was added Tf2O (28.0 g, 99.2 mmol) dropwise at room temperature and the reaction was stirred for 1 hour. The resulting mixture was quenched with water (100 mL) followed by a standard aqueous/EtOAc workup. The residue was purified by silica gel column chromatography (PE:EtOAc=20:1) to give the product as a colorless oil (17.0 g, yield 91%).

Provenance & Evidence