5-CYCLOHEXADECEN-1-ONE is commercially available as a
40 : 60 mixture of its (Z)- and (E)-isomers. It is a colorless liquid with an intense
musk odor.
A three-step synthesis starts from cyclododecanone. Reaction with chlorine
gives 2-chlorocyclododecanone, which is reacted with 2 mol of vinyl magnesium
chloride to give 1,2-divinylcyclododecan-l-ol. This is finally converted into
5-cyclohexadecen-1-one by an oxy-Cope rearrangement.
5-Cyclohexadecen-l-one can be added to perfume compositions as a substitute
for the natural macrocyclic ketone musks：
