Acetylene → HCID 13434207, compound

Participants

Reaction Steps

A solution of 200 ml of octanoyl chloride (A6, R1 =C2H5) in 750 ml of carbon tetrachloride is cooled on an ice bath and treated with 214 g of aluminium chloride in three portions over a 1 hour period while acetylene is bubbled through the solution. The ice bath is removed and the reaction mixture stirred at room temperature for 3 hours with additional acetylene being added. At the end of this period, the reaction mixture is poured into 4 kg of ice. The organic layer is separated and the aqueous layer extracted twice with 500 ml of chloroform. The combined organic extracts are washed once with 500 ml of water, dried over anhydrous sodium sulfate and concentrated in vacuo. Distillation of the residue yields 142 g of trans-1-chloro-dec-1-en-3-one, (A5, R1 =C2H5).

Provenance & Evidence