Oxalyl chloride → Cinnamic Acid

Participants

Reaction Steps

To a solution of 3.05 g. of trans-cinnamic acid in dry benzene is added 5 ml of oxalyl chloride. The reaction mixture is stirred at room temperature, under nitrogen, for 2 hours. Solvent is removed in vacuo and replaced by fresh dry benzene and 3.9 ml. of cyclopropanemethyl alcohol is added. The reaction mixture is stirred overnight at room temperature, under nitrogen. The reaction is worked up by washing with water and brine, drying over calcium sulfate and evaporating under reduced pressure and fractionally distilling to yield the cyclopropanemethyl ester of trans-cinnamic acid, (cyclopropanemethyl trans-cinnamate) b.p. 100° (bath) at .1 mm.

Provenance & Evidence