3-Phenylprop-2-Enal → HCID 72281739, compound

Participants

Reaction Steps

Sodium hydroxide (128.0 g, 3.2 mol) is dissolved in water (1400 mL) and ethanol (675 mL). Cinnamaldehyde (66.1 g, 0.5 mol) and 4-acetylbenzoic acid (82.1 g, 0.5 mol) are added and the mixture stirred for about 5 min. A thick precipitate is formed and the thick mixture is diluted with water (750 mL) and ethanol (750 mL). Stir at room temperature for 18 h. The reaction is cooled and acidified with concentrated HCl (270 mL). The mixture is extracted with ethyl acetate (3×). The combined organic portions are washed with water (2×), dried over Na2SO4, filtered and evaporated. The resulting solid is recrystallized from 2-methoxyethanol and washed with diethyl ether to obtain 36.1 g (26%) of yellow crystals. m.p.=210-214° C.; Anal. Calcd for C18H14O3: C, 77.68; H, 5.07. Found: C, 77.47; H, 5.09.

Provenance & Evidence