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

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.

1. temperaturebeing cooled, until the starting materials
2. customIt is then decanted
3. customthe organic phase is recovered
4. washThe reaction medium is then washed a second time with the saturated aqueous salt solution
5. customthe organic phase is recovered
6. dry with materialThe organic phase is dried over anhydrous magnesium sulphate
7. customthe solvent is removed by evaporation under reduced pressure (20 mmHg) and at a temperature of 30° C
8. additionA mixture of (3E,5Z)-1,3,5-undecatriene (I)

ORD record

ord-7e829cdbdec3450a81a4a59f0e327b2e

Source dataset

uspto-grants-1987_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04652692