3-Phenylprop-2-En-1-Ol → 3-Phenylprop-2-Enal

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Reaction Steps

To 10 ml of dichloromethane is added 0.5 g. (3.73 mmoles) of cinnamyl alcohol. The resulting mixture is added to a stirred suspension of 3.37 g. (11.5 mmoles) of 2,2'-bipyridinium chlorochromate in 15 ml of dichloromethane. The resulting mixture is stirred for four hours after which 15 ml of anhydrous ether is added. The resulting product is filtered through a Hirsch funnel packed 1-2 cm deep with Celite® using ether as a wash solvent. The resulting clear filtrate is washed with 5% hydrochloric acid and 10% sodium carbonate, and dried over sodium sulfate. The drying agent is removed and the solvent evaporated giving a product which is a slightly yellow oil. This oil is then distilled via Kugelrohr to yield pure cinnamaldehyde in a typical yield of 0.323 g. which is 86% of theoretical yield.

Provenance & Evidence