(3,4,5-Tris(benzyloxy)phenyl)methanol → 3,4,5-Tribenzyloxybenzaldehyde

Participants

Reaction Steps

To a solution of 3,4,5-tribenzyloxy-benzyl alcohol 5 (8.9 g, 21 mmol) in methylene chloride (200 mL) at 0° C. was added pyridinium chlorochromate (5.43 g, 25 mmol) in small portions with vigorous stirring. The cooling was discontinued and reaction stirred at room temperature for 4 h. The dark brown suspension was filtered over a long pad of silica gel in a sintered glass funnel, and eluted with CH2Cl2, until all the pure product eluted out. The organic filtrate was evaporated down to give the pure product 6 as a soft white solid (8.1 g, 91.5% yield). 1H NMR (300 MHz, CDCl3): δ 5.16 (s, 6H, OCH2), 7.18 (s, 2H, 2,6-Ar—H), 7.26 -7.41 (m, 15H, Ar—H), 9.80 (s, 1H, CHO).

Provenance & Evidence