A process for process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate of the following formula (3), wherein Ac represents an acetyl group, the process comprising steps of: preparing a nucleophilic reagent, 5-isopropenyl-2-methyl-8-nonenyl compound, of the following general formula (1): wherein M.sup.1 represents Li, MgZ.sup.1, ZnZ.sup.1, Cu, CuZ.sup.1, or CuLiZ.sup.1, wherein Z.sup.1 represents a halogen atom or a 5-isopropenyl-2-methyl-8-nonenyl group, from a 5-isopropenyl-2-methyl-8-nonenyl halide compound of the following general formula (4): wherein X.sup.1 represents a halogen atom; subjecting the nucleophilic reagent (1), 5-isopropenyl-2-methyl-8-nonenyl compound, to an addition reaction with at least one electrophilic reagent selected from the group consisting of formaldehyde, paraformaldehyde, and 1,3,5-trioxane, followed by a hydrolysis reaction to form 6-isopropenyl-3-methyl-9-decenol of the following formula (2); and acetylating 6-isopropenyl-3-methyl-9-decenol (2) to form 6-isopropenyl-3-methyl-9-decenyl acetate (3). ##STR00001##

A process for process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate of the following formula (3), wherein Ac represents an acetyl group, the process comprising steps of: preparing a nucleophilic reagent, 5-isopropenyl-2-methyl-8-nonenyl compound, of the following general formula (1): wherein M.sup.1 represents Li, MgZ.sup.1, ZnZ.sup.1, Cu, CuZ.sup.1, or CuLiZ.sup.1, wherein Z.sup.1 represents a halogen atom or a 5-isopropenyl-2-methyl-8-nonenyl group, from a 5-isopropenyl-2-methyl-8-nonenyl halide compound of the following general formula (4): wherein X.sup.1 represents a halogen atom; subjecting the nucleophilic reagent (1), 5-isopropenyl-2-methyl-8-nonenyl compound, to an addition reaction with at least one electrophilic reagent selected from the group consisting of formaldehyde, paraformaldehyde, and 1,3,5-trioxane, followed by a hydrolysis reaction to form 6-isopropenyl-3-methyl-9-decenol of the following formula (2); and acetylating 6-isopropenyl-3-methyl-9-decenol (2) to form 6-isopropenyl-3-methyl-9-decenyl acetate (3). ##STR00001##

Compounds of formula I

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a process for preparation of compounds of formula I; precursor compounds of formula II

##STR00002##

a process for preparation of precursor compounds of formula II; compounds of formula III

##STR00003##

a process for the preparation of compounds of formula IV from compounds of formula III

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and the use of compounds of formula I for the preparation of compounds of formula IV.

Compounds of formula I

##STR00001##

a process for preparation of compounds of formula I; precursor compounds of formula II

##STR00002##

a process for preparation of precursor compounds of formula II; compounds of formula III

##STR00003##

a process for the preparation of compounds of formula IV from compounds of formula III

##STR00004##

and the use of compounds of formula I for the preparation of compounds of formula IV.

An inexpensive, stereoselective synthesis for nootkatone, tetrahydronootkatone, and their derivatives is disclosed utilizing ozonolysis. The starting materials used in the synthesis are inexpensive and the reactions are commercially feasible and amenable to scaling up. The principal starting material, ()--Pinene, is on the GRAS list (generally recognized as safe).

An inexpensive, stereoselective synthesis for nootkatone, tetrahydronootkatone, and their derivatives is disclosed utilizing ozonolysis. The starting materials used in the synthesis are inexpensive and the reactions are commercially feasible and amenable to scaling up. The principal starting material, ()--Pinene, is on the GRAS list (generally recognized as safe).

An inexpensive, stereoselective synthesis for nootkatone, tetrahydronootkatone, and their derivatives is disclosed utilizing ozonolysis. The starting materials used in the synthesis are inexpensive and the reactions are commercially feasible and amenable to scaling up. The principal starting material, ()--Pinene, is on the GRAS list (generally recognized as safe).

Methods selectively and efficiently produce 3,7-dimethyl-7-octenol and a carboxylic acid ester thereof. More specifically, a method produces 3,7-dimethyl-7-octenol, including steps of: subjecting a 3-methyl-3-butenyl nucleophilic reagent (2) and a 1,3-dihalo-2-methylpropane compound (3) to a coupling reaction to obtain a 2,6-dimethyl-6-heptenyl halide compound (4); converting the compound (4) into a 2,6-dimethyl-6-heptenyl nucleophilic reagent (5); and subjecting the nucleophilic reagent (5) to an addition reaction with at least one electrophilic reagent selected from the group made of formaldehyde, paraformaldehyde and 1,3,5-trioxane, followed by a hydrolysis reaction to obtain 3,7-dimethyl-7-octenol (6); and the other method.

##STR00001##

Methods selectively and efficiently produce 3,7-dimethyl-7-octenol and a carboxylic acid ester thereof. More specifically, a method produces 3,7-dimethyl-7-octenol, including steps of: subjecting a 3-methyl-3-butenyl nucleophilic reagent (2) and a 1,3-dihalo-2-methylpropane compound (3) to a coupling reaction to obtain a 2,6-dimethyl-6-heptenyl halide compound (4); converting the compound (4) into a 2,6-dimethyl-6-heptenyl nucleophilic reagent (5); and subjecting the nucleophilic reagent (5) to an addition reaction with at least one electrophilic reagent selected from the group made of formaldehyde, paraformaldehyde and 1,3,5-trioxane, followed by a hydrolysis reaction to obtain 3,7-dimethyl-7-octenol (6); and the other method.

##STR00001##

Methods selectively and efficiently produce 3,7-dimethyl-7-octenol and a carboxylic acid ester thereof. More specifically, a method produces 3,7-dimethyl-7-octenol, including steps of: subjecting a 3-methyl-3-butenyl nucleophilic reagent (2) and a 1,3-dihalo-2-methylpropane compound (3) to a coupling reaction to obtain a 2,6-dimethyl-6-heptenyl halide compound (4); converting the compound (4) into a 2,6-dimethyl-6-heptenyl nucleophilic reagent (5); and subjecting the nucleophilic reagent (5) to an addition reaction with at least one electrophilic reagent selected from the group made of formaldehyde, paraformaldehyde and 1,3,5-trioxane, followed by a hydrolysis reaction to obtain 3,7-dimethyl-7-octenol (6); and the other method.

##STR00001##