Acetic Acid → n-Butyl cyclopentadiene

Participants

Reaction Conditions

Reaction Steps

A solution of bromobutane (0.98 mol) in 28 grams of THF is heated to 60-65° C. A warm solution of CpMgCl in THF (1.0 mol) as produced in Example 1 is added to the bromobutane solution while maintaining a pot temperature between 60-65° C. After the addition and the consequent reaction are complete by GC analysis, the reaction mixture is cooled to ambient temperature, 25% by weight of aqueous acetic acid is added, and the organic layer is separated, washed with 10% by weight of aqueous sodium carbonate, and dried over anhydrous sodium sulfate. The organic layer is filtered, and fractionally distilled under reduced pressure to recover 70 to 80% yield of n-butyl cyclopentadiene.

Provenance & Evidence