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

Participants

Reaction Conditions

Reaction Steps

1.3 millimoles of nickel (2+) bis(triphenylphosphine) bromide and 100 millimoles of magnesium 1-heptenyl bromide (mixture of two isomers Z and E in a ratio by weight of 6:4), dissolved in tetrahydrofuran, are added, under nitrogen and while cooling, to a solution of 50 millimoles of (E)-1-chloro-1,3-butadiene in 200 ml of tetrahydrofuran. The mixture is heated at 35° C. for approximately 1 hour and the reaction medium is then hydrolysed with a saturated ammonium chloride solution. The mixture is decanted. The organic phase is washed twice with 25 ml of the saturated aqueous solution each time. The organic phase is dried over anhydrous magnesium sulphate. 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. The mixture is distilled under reduced pressure (0.02 mmHg) and at a temperature of 30° C. in order to obtain a pure mixture of two isomers in a ratio by weight of 6:4.

Provenance & Evidence