Diethyl Ether → 5-Norbornene-2-carboxylic acid

Participants

Reaction Steps

Freshly distilled cyclopenta-1,3-diene (66.11 g) was added to a solution of freshly distilled acrylic acid (73 g, inhibited with p-methoxyphenol) and diethyl ether (75 ml). The solution had a temperature between 5° C. and 10° C. The exothermic reaction that ensued was controlled by an ice bath. The cyclopentadiene was added to the solution over a period of 30 minutes and after all the cyclopentadiene had been added, the solution was allowed to warm to ambient temperature. After a reaction period of 4 hours, gas chromatographic (GC) analysis indicated a yield of 100 percent of theory of the carboxylic acid. The carboxylic acid was recovered from the diethyl ether by vacuum distillation.

Provenance & Evidence