The present invention is related to a novel and improved process for the production of dehydrolinalyl acetate (DLA), which IUPAC name is acetic acid 1-ethynyl-1,5-dimethyl-hex-4-enyl ester, starting from dehydrolinalool (DLL), which IUPAC name is 3,7-dimethyloct-6-en-1-yn-3-ol, by acetylation.

The present invention is related to a novel and improved process for the production of dehydrolinalyl acetate (DLA), which IUPAC name is acetic acid 1-ethynyl-1,5-dimethyl-hex-4-enyl ester, starting from dehydrolinalool (DLL), which IUPAC name is 3,7-dimethyloct-6-en-1-yn-3-ol, by acetylation.

The present invention relates to novel cyclopropane derivatives represented by Formula I:

##STR00001##

wherein R represents a hydrocarbon group containing 1-20 carbon atoms or an ester containing 1-20 carbon atoms;

wherein R′ represents a C.sub.1-C.sub.6 acyclic carboxylic acid ester, a C.sub.4-C.sub.6 cyclic carboxylic acid ester or —OR″, and R″ is selected from the group consisting of H, a C.sub.1-C.sub.6 acyclic hydrocarbon group, a C.sub.3-C.sub.6 carbocyclic ring and a C.sub.4-C.sub.5 heterocyclic ring; and

wherein the composition is selected from the group consisting of a flavor composition and a fragrance composition.

In one aspect, the invention provides a method for synthesizing a fatty olefin derivative. The method includes: a) contacting an olefin according to Formula I

##STR00001##

with a metathesis reaction partner according to Formula IIb

##STR00002##

in the presence of a metathesis catalyst under conditions sufficient to form a metathesis product according to Formula IIIb:

##STR00003##

and
b) converting the metathesis product to the fatty olefin derivative. Each R.sup.1 is independently selected from H, C.sub.1-18 alkyl, and C.sub.2-18 alkenyl; R.sup.2b is C.sub.1-8 alkyl; subscript y is an integer ranging from 0 to 17; and subscript z is an integer ranging from 0 to 17. In certain embodiments, the metathesis catalyst is a tungsten catalyst or a molybdenum catalyst. In various embodiments, the fatty olefin derivative is a pheromone. Pheromone compositions and methods of using them are also described.

In one aspect, the invention provides a method for synthesizing a fatty olefin derivative. The method includes: a) contacting an olefin according to Formula I

##STR00001##

with a metathesis reaction partner according to Formula IIb

##STR00002##

in the presence of a metathesis catalyst under conditions sufficient to form a metathesis product according to Formula IIIb:

##STR00003##

and
b) converting the metathesis product to the fatty olefin derivative. Each R.sup.1 is independently selected from H, C.sub.1-18 alkyl, and C.sub.2-18 alkenyl; R.sup.2b is C.sub.1-8 alkyl; subscript y is an integer ranging from 0 to 17; and subscript z is an integer ranging from 0 to 17. In certain embodiments, the metathesis catalyst is a tungsten catalyst or a molybdenum catalyst. In various embodiments, the fatty olefin derivative is a pheromone. Pheromone compositions and methods of using them are also described.

The present invention relates to a new dehydrogenation process of specific compounds.

The present invention relates to a new dehydrogenation process of specific compounds.

The present invention relates to a process for preparing a 3-isopropenyl-6-heptenal compound of the following formula (2): wherein R.sup.1 represents a hydrogen atom or a methyl group, the process comprising: subjecting a 3-isopropenyl-6-heptenoate ester compound of the following formula (1): wherein R.sup.1 is as defined above, and R.sup.2 represents a monovalent hydrocarbon group having 1 to 10 carbon atoms, to a reduction reaction with a reducing agent to form the 3-isopropenyl-6-heptenal compound (2).

##STR00001##

The present invention relates to a process for preparing a 3-isopropenyl-6-heptenal compound of the following formula (2): wherein R.sup.1 represents a hydrogen atom or a methyl group, the process comprising: subjecting a 3-isopropenyl-6-heptenoate ester compound of the following formula (1): wherein R.sup.1 is as defined above, and R.sup.2 represents a monovalent hydrocarbon group having 1 to 10 carbon atoms, to a reduction reaction with a reducing agent to form the 3-isopropenyl-6-heptenal compound (2).

##STR00001##

Suggested is a fragrance mixture comprising specific esters of (−)-carveol and/or (−)-dihydro-carveol.