(E)-2-buten-1-ol mesylate → 1-chloro-(Z,E)-7,10-dodecadiene

Participants

Reaction Steps

The synthetic procedure was about the same as in Example 1 excepting replacement of 271.5 g of (E)-2-butenyl chloride with 450 g (3 moles) of (E)-2-buten-1-ol mesylate which were added dropwise to the reaction mixture kept at 30° C. or below followed by further continued agitation of the reaction mixture at 30° C. for 1.5 hours to effect hydrolysis so that 216 g of 1-chloro-(E)-10-dodecen-7-yne were obtained in a purity of 94%. The yield was 35% of the theoretical value. Partial hydrogenation of this ene-yne compound in the same manner as in Example 1 gave 203 g of 1-chloro-(Z,E)-7,10-dodecadiene in a purity of 88%. The yield was 88% of the theoretical value.

Provenance & Evidence