Substituted acetonaphthones, processes for preparing same, uses of same in perfumery, and intermediates used in said processes

Abstract

Abstract Described are hexahydrotetramethyl acetonaphthones and mixtures of such substituted acetonaphthones having the generic formula: ##STR1## wherein one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines is a carbon-carbon single bond, and, specifically, the novel isomer having the structure: ##STR2## and processes for the preparation of such mixtures and said novel isomer, as well as a known single component of said mixtures and compounds, by means of first forming 3-chloromesityl oxide from mesityl oxide and chlorine and then reacting the 3-chloromesityl oxide with myrcene via a Diels-Alder reaction thereby producing a chlorine containing Diels-Alder adduct and then either: (i) dehydrochlorinating the chlorine containing Diels-Alder adduct to form an acetyl conjugated cyclohexadiene and cyclizing the acetyl conjugated cyclohexadiene to produce a mixture of isomers having the generic formula: ##STR3## wherein one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines is a carbon-carbon single bond; or (II) CYCLIZING THE CHLORINE CONTAINING Diels-Alder adduct to form an acetyl-chloro octahydronaphthalene and dehydrochlorinating the acetylchloro octahydronaphthalene to form a composition substantially composed of a compound having the structure: ##STR4## The products produced are useful as vetiver ingredients in perfumes and perfumed articles.

Inventors

• 👤 William L. Schreiber
• 👤 James N. Siano
• 👤 Edward J. Shuster

Bibliographic Details