Acetic Acid → m-Ethylbenzaldehyde

Participants

Reaction Steps

Add a 1 M solution of diisobutylaluminum hydride in toluene (76 mmol) dropwise to a solution of m-ethylbenzonitrile (38 mmol) in toluene (50 mL) under nitrogen in a dry ice-acetone bath. Stir for 30 minutes then add acetic acid (20 mL) dropwise followed by water (100 mL). Stir the reaction for 2 hours. Separate the layers and extract the aqueous with toluene. Dry the combined organic layers over sodium sulfate, and evaporate to give the title compound (4.5 g, 88% yield). 1HNMR (400.43 MHz, CDCl3): δ 9.97 (s, 1H), 7.69-7.66 (m, 2H), 7.46-7.40 (m, 2H), 2.71 (q, J=7.6 Hz, 2H), 1.25 (t, J=7.5 Hz, 3H).

Provenance & Evidence