Ethyl Acrylate → Ethyl 4-pentyl-3-cyclohexen-l-carboxylate

Participants

Reaction Conditions

Reaction Steps

Ethyl acrylate (1.92 ml) is added to toluene (15 ml) and aluminum chloride (215 mg). The resulting solution is cooled to 0° C., after which 2-pentyl-1,3-butadiene (2.0 g) is added dropwise over a period of 30 minutes. The reaction mixture is then stirred for 5 hr at 0° C., and stored in a 4° C. refrigerator overnight. The resulting mixture is placed in an extraction funnel, and washed with two 200 ml aliquots of 1% HCl. The reaction mixture is further washed with 100 ml water, then with 100 ml saturated sodium chloride, and dried over a combination of sodium sulfate and potassium carbonate. The mixture is filtered through celite, and the solvent removed in vacuo. The resulting liquid is distilled at 107°-109° C. at 1 mm Hg to produce ethyl 4-pentyl-3-cyclohexen-1-carboxylate.

Provenance & Evidence