Zur Kenntnis des Kohlenstoffringes XXVIII. Über die Herstellung von 2‐Methyl‐, 3‐Methyl‐ und 7‐Methyl‐cyclopentadecanon‐(1). Beiträge zur Synthese des d, l‐Muscons

Structure−Odor Relationships

“…Since examples of musk odorants were found in all four chemical classes they concluded that a CO group was a necessary feature of the ring for musk odor but that the manner of its linkage was not important. One year later Ruzicka demonstrated that the “required” CO could in fact be substituted by a ring NH group. A few macrocyclic ethers, sulfides, and pyridines have subsequently been reported to have a musk odor.…”

Synthesis of (±)-Muscone from Ethyl 6-Methyl-8-oxopentadecanedioate

“…After a stirring period of 4 hr at room temperature, water (20 ml) and then sodium carbonate (0.5 g) was added to the mixture; the solution was extracted with benzene (30 ml x 2). 9,9-Ethylenedioxy-7-methylcyclopentadec-1-ene (6) In a 50 ml sealed tube were placed 5 (1.2 g), sodium iodide (0.9 g, 6 mmole), zinc dust (0.26 g, 4 mg-atom) and dry, N,N-dimethylformamide (12 ml). This tube was heated in an oil bath (170~175°C) for 2.5 hr with an occasional shaking.…”

“…In a search for a more practical approach, *3 it was found that conversion of vic-ditosyloxy derivative (5) into the alkene (6) was achieved by treatment of 5 with sodium iodide and excess of zinc dust in boiling N,N-dimethylformamide (TipsonCohen procedure), a procedure used for the introduction of unsaturation into acyclic I81 and cyclicl9.201 vic-ditosylates. The product 6 obtained by this procedure was significantly easier to purify than that obtained by the other methods.…”