Veratraldehyde → (3,4-Dimethoxyphenyl)(hydroxy)acetonitrile

Participants

Reaction Steps

To 3,4-dimethoxybenzaldehyde (1.66 g, 10 mmol) in ethyl acetate (20 mL) was added NaHSO3 (5.2 g, 50 mmol) in water (20 mL), followed by potassium cyanide (3.26 g, 50 mmol) in water (20 mL). The mixture was stirred overnight at rt, then warmed to 50° C. for 6 h. The reaction was cooled to rt, diluted with ethyl acetate, and the layers were separated. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated. The resulting residue was purified via silica gel chromatography (0-50% ethyl acetate/hexanes) to provide 137A (1.25 g, 65%) and starting material (0.52 mg). LC-MS: 176.22 (M−H2O)+.

Provenance & Evidence