3-Phenylprop-2-Enal → HCID 18177470, compound

Participants

Reaction Steps

3.8 g (25 mmol) of 2-hydroxy-5-methoxybenzaldehyde are added to a solution of 3.63 g (27.5 mmol) of cinnamaldehyde in 25 ml of N,N-dimethylformamide; 3.8 g (27.5 mmol) of potassium carbonate are then added to the medium. After 10 minutes of reflux, the reaction mixture is concentrated in vacuo; the residue is then taken up in water. The aqueous phase is extracted with ethyl acetate; the organic phase is then dried over magnesium sulphate. After evaporation of the solvent in vacuo, the crude product is dissolved in 30 ml of anhydrous ethanol; 0.95 g (25 mmol) of sodium borohydride is then added to the medium. The solution is stirred under argon for 15 minutes; the solvent is then evaporated in vacuo. The residue obtained is dissolved in water and then hydrolysed with a 1N hydrochloric acid solution. The aqueous phase is extracted with ethyl acetate; the organic phase is then dried over magnesium sulphate. After evaporation of the solvent in vacuo, chromatography on a silica column (eluant:AcOEt/PE:30/70 then 40/60) yields the title alcohol in the form of a yellow solid in a yield of 47%.

Provenance & Evidence