Triacetoxyperiodinane → 3-(3-Methoxypropyl)benzaldehyde

Participants

Reaction Steps

To a CH2Cl2 solution (0.3 M) of [3-(3-methoxypropyl)phenyl]methanol from the previous step (1 eq.) was added Dess-Martin periodinane (1.2 eq.). The resulting suspension was stirred at RT for 2 h. The reaction was quenched with sat. aq. NaHCO3 and 2 N aq. Na2S2O3. The biphasic mixture was allowed to stir at RT for 20 min, poured into sat. aq. NaHCO3 and extracted with CH2Cl2. The combined organic extracts were washed with brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded a cloudy oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, Hex→7:3 (v/v) Hex:EtOAc) afforded the title compound as a colorless oil.

Provenance & Evidence