4-Methoxybenzaldehyde → 4-Methoxybenzyl alcohol

Participants

Reaction Steps

A 30-mL eggplant flask equipped with a magnetic stirrer was heat dried while pumping to a vacuum of 5 Pa before its interior was purged with nitrogen atmosphere. To the flask, 4-methoxybenzaldehyde (140 mg, 1.0 mmol) and 1,1,1,3,3-pentamethyldisiloxane (371 mg, 2.5 mmol) were added through a syringe, and iron complex A (5 mg, 0.01 mmol) was admitted as catalyst. The solution was stirred at room temperature for 3 hours. At 0° C., THF (1 mL) and tetrabutylammonium fluoride in THF (1 M, 1 mL) were then added to the solution, which was stirred at 0° C. for 1 hour. THF was distilled off in vacuum. The crude product was purified by silica gel-packed column chromatography using hexane/ethyl acetate (3/1) as developing solvent, obtaining 4-methoxybenzyl alcohol (131 mg, 0.95 mmol, 95%). The results as are shown as Entry 2 in Table 6. The resulting alcohol was identified for geometry by 1H and 13C-NMR spectroscopy.

Provenance & Evidence