Acetic Acid → HCID 11804741, compound

Participants

Reaction Steps

2.5 eq. (20.47 g, 0.31 mol) of cyclopentadiene and diethylamine (7.44 g, 1.102 mol) were added to butylaldehyde (8.93 g, 0.124 mol). The reactant solution was incubated in 80 ml of methanol and then at room temperature for 2 hours. 15.1 ml of acetic acid was added, and the result was stirred for 10 minutes. The resultant solution was then diluted with 200 ml of pentane and treated with 100 ml of water to remove methanol. To remove residual diethylamine, the resultant solution was washed with 200 ml of 1 N HCl for 30 seconds and neutralized with 200 ml of saturated sodium bicarbonate. An organic layer was washed with a NaCl solution, subjected to solvent removal in a rotary evaporator, and distilled at 40° C., to give 5-butylidene-cyclopenta-1,3-diene (yield: 96%).

Provenance & Evidence