Cyclialkylation of aromatics with isoprene Musks to herbicides

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I Background

It has been said that no successful perfume has been compounded without the use of musk. As Carpenter said, “There is hardly a type from the simplest of colognes to the most subtle and sophisticated of orientals that does not benefit by the inclusion of some musk.” Originally, of course, perfumers were dependent on natural sources for musk fixatives. The most prized was Tonquin musk, derived from the musk-deer of Asia.

It is now almost 90 years since Albert Baur made the surprising discovery that the odor of natural musk is imitated in certain nitrated derivatives of benzene. In 1895, shortly after this discovery, the Givaudan Company was founded in Switzerland to manufacture aroma chemicals and perfume intermediates. The nitro musks were among the earliest products manufactured.

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Baur’s first musk, trinitro-m-t-butyltoluene, marketed as “Musk Baur” (also known as “Musk B," “Tonquinol,” or “Musk Toluene”), was an immediate success, diluted with nine times its weight of acetanilide and selling for about $500 per kilo, or about one-half the then current price for natural Tonquin musk. Baur’s discovery had a tremendous impact on the emerging synthetic aromatics industry and stimulated much research in the area. His discovery was followed in rapid order by three other nitromusks which are still widely used and often referred to as the “workhorses” of the synthetic musks. Baur’s original musk was soon replaced by musk xylol, and is no longer used.