Syntheses of Racemic Muscone

One of the first industrial muscone syntheses stems from work at BASF. [182] Analogous to the synthesis of exaltone, cyclododecanone is converted, by reaction with but-3-yn-2-ol, into a diol, which is further transformed by a Meyer-Schuster rearrangement and Nazarov cyclisation into a methyl-substituted bicycle. A very short route to the same product was described by Mitsui Petrochemical Industries a few years later this involved the direct conversion of cy-clododecene with crotonic acid in the presence of polyphosphoric acid, and resulted in a remarkable yield of 54 %. [183] 

Muscone is then prepared by the following sequence reduction to the aUyl alcohol, ozonolysis of the double bond, Wolff-Kishner reduction of both carbonyl groups, and Jones oxidation. The overall yield is around 40 % based on cydodo-decanone. 

Although the process is industrially feasible, the ozonolysis requires special equipment, and poses potential hazard. 

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