Ammonia → 7-(4-Octylphenyl)hept-5-ynoic acid

Participants

Reaction Steps

A solution of lithium amide in liquid ammonia is prepared by the addition of lithium metal (2 mmoles) to liquid ammonia containing a trace amount of ferrous sulfate. To this solution is added 4-chlorobutyric acid (1 mmole) and p-(n-octyl)benzylacetylene (1 mmole, prepared as described in paragraph B of this example). After a suitable time at refluxing liquid ammonia temperatures, the ammonia is removed by evaporation and the residue dissolved in 10% sodium hydroxide solution. After extraction with ether, the aqueous layer is acidified to a pH of 2-3 with concentrated hydrochloric acid, and extracted with methylene chloride. The methylene chloride layer is separated and the solvent removed by evaporation to give a residue. This residue is purified either by column chromatography or molecular distillation under reduced pressure to afford the desired title product, 7-[p-(n-octyl)phenyl]hept-5-ynoic acid.

Provenance & Evidence