3-Phenylprop-2-Enal → HCID 13595926, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 19.6 mL (20.0 grams, 149 mmol) of cinnamaldehyde, 40.6 grams (298 mmol) of potassium carbonate, and 150 mL of ether was cooled to −60° C. and treated with a prechilled (−78° C.) solution of 17.8 mL (13.5 grams, 300 mmol) of liquid dimethylamine, condensed from the gas at −78° C., in 20 mL of ether. After stirring for 0.5 hours at −60° C., the mixture was allowed to slowly warm to room temperature and then stirred for an additional 3 hours. The mixture was filtered, concentrated, and distilled to give 10.2 grams (42% yield) of the title compound as a yellow liquid, bp 95-100° C./2.8-3.0 Torr. The liquid slowly polymerized on standing and was used directly. 1H NMR (CDCl3) d 2.57 (6H, s), 3.30 (2H, d, J=7 Hz), 4.35 (1H, dt, J=7, 14 Hz), 5.99 (1H, dt, J=1, 14 Hz), 7.15-732 (5H, m).

Provenance & Evidence