Ammonium Chloride → (3E,5E)-1,3,5-Undecatriene

Participants

Reaction Steps

100 millimoles of magnesium 1-heptenyl bromide (mixture of two isomers Z and E in a ratio by weight of 50% and 50%) are added to a solution of 50 millimoles of (E)-1,3-butadiene butyl sulphide and 3.25 millimoles of nickel (2+) bis(triphenylphosphine) bromide in 200 ml of tetrahydrofuran. The reaction is allowed to proceed, without the reaction medium being cooled, until the starting materials have disappeared completely. The mixture is then hydrolysed with 100 ml of a saturated ammonium chloride solution or another saturated aqueous salt solution. The mixture is stirred for one hour. It is then decanted and the organic phase is recovered. The reaction medium is then washed a second time with the saturated aqueous salt solution and the organic phase is recovered. The organic phase is dried over anhydrous magnesium sulphate and the solvent is removed by evaporation under reduced pressure (20 mmHg) and at a temperature of 30° C. A mixture of (3E,5Z)-1,3,5-undecatriene (I) and (3E,5E)-1,3,5-undecatriene (II) is obtained. This mixture is distilled in the presence of an antioxidant under reduced pressure (0.05 mmHg) and at a temperature of 35° C. in order to obtain a pure mixture of compounds of the formulae I and II.

Provenance & Evidence