Vanillin → HCID 136138631, compound

Participants

Reaction Steps

In 62.9 g of acetic anhydride, 26.73 g of 4-methylquinoline and 31.25 g of vanillin were refluxed overnight. The resultant reaction mixture was treated with an alkali. The product thus obtained was recrystallized via butyl cellosolve, to afford 29 g of 4-[2-(4-hydroxy-3-methoxyphenyl)-ethenyl]-quinoline having a melting point of 217°-219° C. From 0.55 g of this product, 1.75 g of triethylamine, 1.66 g of methacrylic acid chloride, and 16 cm3 of N,N-dimethylacetamide, there was obtained 4.70 g (80.3% in yield) of 4[2-(4-methacroyloxy-3-methoxyphenyl)-ethenyl]-quinoline having a melting point of 134°-135° C. This product was recrystallized via ethyl acetate and assayed by infrared absorption spectrometry and elementary analysis for its chemical structure.

Provenance & Evidence