tert-Butanol → 2-Chloro-3,5-dimethoxybenzaldehyde

Participants

Reaction Steps

To a suspension of Dess-Martin periodinane (1.38 g, 32.5 mmol) in CH2Cl2 (120 mL) was added tert-butanol (3.05 mL, 32.5 mmol). After stirring for 15 min, a sol. of 2-chloro-3,5-dimethoxybenzyl alcohol (H. Newman, R. B. Angier, J. Org. Chem., 1966, 31, 1462-1464, 5.06 g, 25.0 mmol) in CH2Cl2 (20 mL) was added. After stirring for 1 h, EtOAc (200 mL) was added and the mixture was washed with aq. 1M NaOH. The org. phase was evaporated, and the crude product was dissolved again in EtOAc (200 mL), and washed successively with aq. 1M NaOH (2×), water (2×) and brine. The org. phase was dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. The aldehyde was used without further purification. LC-MS: tR=0.92 min.

Provenance & Evidence