Hydrochloric Acid → Cinnamic Acid

Participants

Reaction Steps

Combine 312 g (2.99 mole) of malonic acid, 506 mL of pyridine, 30 mL of piperidine and 300 g (1.49 mole) of p-methylsulfonyl-benzaldehyde and heat the mixture to 95°-100° C. for 4 h. Cool the mixture to room temperature and slowly pour into 3 L of a mixture of HCl, water and ice. Collect the resulting precipitate by filtration and dry the solid to give 340 g (83% yield) of the E-cinnamic acid derivative, m.p.=294°-296° C. 1H NMR (DMSO-d6, ppm): 7.96 (s, 4H); 7.78 (d, J=16 Hz, 1H); 6.71 (d, J=16 Hz, 1H); 3.5 (hr. s, 1H); 3.25 (s, 3H). ##STR15##

Provenance & Evidence