Hydrochloric Acid → 4-(2-(4-Formylphenyl)-ethenyl)-pyridine

Participants

Reaction Steps

A mixture of 400 parts of terephthaldehyde, 120 parts of acetic acid and 300 parts of acetic anhydride was refluxed for two hours. 188 parts of 4-picoline were then added over a period of 45 minutes, and the dark brown mixture was refluxed for a further 2 hours. 3300 parts of 1M aqueous hydrochloric acid were then added. The desired product was extracted with toluene and treated with 5M sodium hydroxide to a pH between 5 and 6. The crude solid product was dissolved in hot ethyl acetate and the solution was filtered. Cooling of the filtrate gave the desired product, 4-(2-(4-formylphenyl)-ethenyl)-pyridine.

Provenance & Evidence