Hydrochloric Acid → 4-Carboxychalcone

Participants

Reaction Conditions

Reaction Steps

Sodium hydroxide (128.0 g, 3.2 mol) is dissolved in water (1400 mL) and ethanol (675 mL). The mixture is cooled to 20° C. and acetophenone (120 g, 0.5 mol) is added with mechanical stirring. 4-Carboxybenzaldehyde (75 g, 0.5 mol) and the reaction stirred at room temperature for 6 h. The reaction is acidified with concentrated HCl (300 mL) and extracted with ethyl acetate (3×). The combined organic portions are washed with water, saturated brine, dried, and evaporated in vacuo. The material is recrystallized from isopropanol with a small amount of methanol to obtain 48 g (38%) of the titled compound. m.p.=197-200° C.; Anal. Calcd for C16H12O3: C, 76.18; H, 4.79. Found: C, 76.03; H, 5.05.

Provenance & Evidence