HCID 178478985, Verbindung → HCID 19857657, Verbindung

The experimental procedure was substantially the same as in Example 1 except that the starting Grignard mixture contained 3 moles of 8-bromo-1-octynyl magnesium chloride in tetrahydrofuran in place of 8-chloro-1-octynyl magnesium chloride to give 529 g of 1-bromo-(E)-10-dodecen-7-yne in a purity of 95%. The yield was 69% of the theoretical value. Partial hydrogenation of 150.5 g of this ene-yne compound in the same manner as in Example 1 gave 145 g of a product boiling at 106° to 110° C. under a pressure of 1 mmHg, which could be identified by analysis to be 1-bromo-(Z,E)-7,10-dodecadiene. The analytical data leading to the identification of this product compound were as follows.