Hydrochloric Acid → 4-Ethynyl-2-nitrophenol

Participants

Reaction Conditions

Reaction Steps

In the third step of the process (equation 3), 4-acetoxy-3-nitro-β-chlorocinnamaldehyde is added to a solution of sodium hydroxide. The reaction mixture is maintained at 50° to 80° C. for about 15 to 30 minutes and then cooled at 0° C. In the reaction that occurs, the ester group is hydrolyzed, and hydrogen chloride and carbon monoxide are simultaneously eliminated. The mole ratio of sodium hydroxide to 4-acetoxy-3-nitro-β-chlorocinnamaldehyde is usually about 3 to 10:1. The cooled solution is neutralized with glacial acetic acid to give a precipitate which is separated by filtration. The precipitate is then purified to give crystals of 4-ethynyl-2-nitrophenol.

Provenance & Evidence