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filingDate 1989-02-03-04:00^^<http://www.w3.org/2001/XMLSchema#date>
grantDate 1991-02-05-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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publicationDate 1991-02-05-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber US-4990496-A
titleOfInvention Use of cycloaliphatic ketones as perfuming and flavoring ingredients
abstract Optically active isomers of alpha-damascone of formula <IMAGE> (I) wherein the wavy line designates a C-C bond of cis or trans configuration and its 3-buten-1-one derivative are new compounds having utility in the perfume and flavor industry. They can be prepared starting from an enolate of formula <IMAGE> (II) where the wavy line has the meaning given above and Me designates an alkali metal, preferably lithium or magnesium, by treating said enolate with a bifunctional nitrogen derivative of formula <IMAGE> (III) where the asterisk identifies a center of chirality; index n stands for zero or 1; each of symbols R0 and R1 defines a linear or branched alkyl or aralkyl radical, or one of them represents a hydrogen atom and the other an alkyl radical as defined above; each of symbols R2 and R3 represents a linear or branched alkyl radical, or one of them represents a hydrogen atom and the other an alkyl such as defined above; and Z designates an OH group or a divalent radical of formula HN-C(O), the nitrogen atom of which is bound to the carbon atom at position 3 and the carbonyl group is bound to the nitrogen atom at position 1; and wherein the nitrogen atom at position 1 can be optionally bound to a benzylic group of a polystyrenic resin; hydrolyzing the reaction mixture and isomerizing it by means of an isomerization agent. Cycloaliphatic ketones (I) are also prepared starting from an organo-magnesium compound of formula <IMAGE> (IV) where the wavy line has the above given meaning and X designates a halogen atom, by treating said compound with one equivalent of a lithium alkoxide.
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