Benzaldehyde → 5337-53-1

Participants

Reaction Steps

A solution of NaOH (12.8 mmol, 1.28 equiv.) in water (4.55 g) and ethanol (2.32 g) are introduced into a round bottom flask with a magnetic stirrer. Into the alkaline solution is placed 2-acetyl pyridine 1a (10 mmol, 1 equiv.) and the flask is rapidly surrounded by ice and the stirrer is started. The temperature reaches 10° C.-15° C. and benzaldehyde 1b (10 mmol, 1 equiv.) is added at once. The ice bath is removed and the reaction is stirred for 15 hours. The reaction is filtered. The filtrate is concentrated under reduced pressure and the product is purified by flash column chromatography on SiO2 (33% ethyl acetate/hexanes) to give the 3-phenyl-1-pyridin-2-yl-propenone 1c as a pale yellow solid. See Kohler, E. P. & H. M. Chadwell, H. M., Org. Synth., Coll. Vol. 1, 2nd ed., p. 78.

Provenance & Evidence