Iodine → 6,10-Dimethyl-1,5,9-undecatriene

Participants

Reaction Steps

Degreased magnesium turnings (84 g., 3.5 mole) were suspended in absolute ether (100 ml.). The Mg was activated with one crystal of iodine. In the course of about 3 hours, 300 g. (1.75 mole) of geranyl chloride, then 268 g. (3.5 mole) of allyl chloride in 800 ml. of ether were added dropwise. The mixture was boiled for 4 hours, then it was cooled and poured into a solution of 200 g. of NH4Cl in 1 liter of ice water. The solution was extracted with ether. The extracts were treated as usual, after concentration, they gave 384 g. of crude 6,10-dimethyl-1,5,9-undecatriene which was used without further purification.

Provenance & Evidence