Nitromethane → trans-4-Methoxy-beta-nitrostyrene

Participants

Reaction Conditions

Reaction Steps

To a cool (0° C.), stirred solution of 4-anisaldehyde (1.75 mL, 14.3 mmol), nitromethane (2.0 mL, 36.9 mmol) in MeOH (6.0 mL) was added NaOH (1M, 40 mL), and allowed to warm to room temperature. After 2.5 hours, ice water was added with stirring, extracted with DCM (3×), the combined extracts were dried (MgSO4), filtered, concentrated and purified on Biotage Horizon to provide the product as a solid: 1H NMR (400 MHz, CDCl3) δ ppm: 7.97 (1H, d, J=13.64 Hz), 7.51 (1H, d, J=13.64 Hz), 7.50 (1H, d, J=8.84 Hz), 6.95 (2H, d, J=8.84 Hz), 3.86 (3H, s).

Provenance & Evidence