There are provided methods of efficiently producing compounds that are, for example, sex pheromones of San Jose Scale. For example, there is provided a method for producing a 7-methyl-3-methylene-7-octenyl carboxylate compound (1), the method including the step of coupling a nucleophilic reagent expressed as a 3-methyl-3-butenyl M of General Formula (8):

##STR00001##

wherein M is a cationic moiety, with an acetal compound of General Formula (9):

##STR00002##

wherein R.sup.1 and R.sup.2, which may be the same or different, are each an alkyl group having 1 to 6 carbon atoms, or are bonded to each other to form a divalent alkylene group having 2 to 12 carbon atoms, and X is a leaving group, to obtain the 7-methyl-3-methylene-7-octenal acetal compound.

There are provided methods of efficiently producing compounds that are, for example, sex pheromones of San Jose Scale. For example, there is provided a method for producing a 7-methyl-3-methylene-7-octenyl carboxylate compound (1), the method including the step of coupling a nucleophilic reagent expressed as a 3-methyl-3-butenyl M of General Formula (8):

##STR00001##

wherein M is a cationic moiety, with an acetal compound of General Formula (9):

##STR00002##

wherein R.sup.1 and R.sup.2, which may be the same or different, are each an alkyl group having 1 to 6 carbon atoms, or are bonded to each other to form a divalent alkylene group having 2 to 12 carbon atoms, and X is a leaving group, to obtain the 7-methyl-3-methylene-7-octenal acetal compound.

The present invention is related to a novel and improved process for the preparation of 3,7-dimethylnonan-1-ol.

Provided are a terminal conjugated trienal acetal compound useful as an intermediate for producing a terminal conjugated trienal compound, and a method for producing a terminal conjugated trienal compound through deprotection of the terminal conjugated trienal acetal compound. More specifically, provided are a terminal conjugated trienal acetal compound represented by General Formula (1); a method for producing a (Z,E)-terminal conjugated trienal acetal compound, the method comprising the step of: reacting a phosphonium salt represented by General Formula (7) with (E)-2,4-pentadienal through Wittig reaction to obtain a (Z,E)-terminal conjugated trienal acetal compound represented by General Formula (3); and a method for producing a terminal conjugated trienal compound, the method comprising the step of: deprotecting the terminal conjugated trienal acetal compound represented by General Formula (1) to obtain a terminal conjugated trienal compound represented by General Formula (2).

##STR00001##

Provided are a terminal conjugated trienal acetal compound useful as an intermediate for producing a terminal conjugated trienal compound, and a method for producing a terminal conjugated trienal compound through deprotection of the terminal conjugated trienal acetal compound. More specifically, provided are a terminal conjugated trienal acetal compound represented by General Formula (1); a method for producing a (Z,E)-terminal conjugated trienal acetal compound, the method comprising the step of: reacting a phosphonium salt represented by General Formula (7) with (E)-2,4-pentadienal through Wittig reaction to obtain a (Z,E)-terminal conjugated trienal acetal compound represented by General Formula (3); and a method for producing a terminal conjugated trienal compound, the method comprising the step of: deprotecting the terminal conjugated trienal acetal compound represented by General Formula (1) to obtain a terminal conjugated trienal compound represented by General Formula (2).

##STR00001##

The present invention provides a process for preparing (9Z,11E)-9,11-hexadecadienal of the following formula (4), the process comprising: subjecting (2E)-2-heptenal of the following formula (1) to a Wittig reaction with a triarylphosphonium 9,9-dialkoxynonylide compound of the following general formula (2), wherein Ar represents an aryl group that may be same with or different from each other, and R.sup.1 and R.sup.2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R.sup.1 and R.sup.2 may form together a divalent hydrocarbon group, R.sup.1-R.sup.2, having 2 to 10 carbon atoms to form a (5E,7Z)-16,16-dialkoxy-5,7-hexadecadiene compound of the following general formula (3), wherein R.sup.1 and R.sup.2 are as defined above; and hydrolyzing the (5E,7Z)-16,16-dialkoxy-5,7-hexadecadiene compound (3) to form (9Z,11E)-9,11-hexadecadienal (4).

##STR00001##

The present invention provides a process for preparing (9Z,11E)-9,11-hexadecadienal of the following formula (4), the process comprising: subjecting (2E)-2-heptenal of the following formula (1) to a Wittig reaction with a triarylphosphonium 9,9-dialkoxynonylide compound of the following general formula (2), wherein Ar represents an aryl group that may be same with or different from each other, and R.sup.1 and R.sup.2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R.sup.1 and R.sup.2 may form together a divalent hydrocarbon group, R.sup.1-R.sup.2, having 2 to 10 carbon atoms to form a (5E,7Z)-16,16-dialkoxy-5,7-hexadecadiene compound of the following general formula (3), wherein R.sup.1 and R.sup.2 are as defined above; and hydrolyzing the (5E,7Z)-16,16-dialkoxy-5,7-hexadecadiene compound (3) to form (9Z,11E)-9,11-hexadecadienal (4).

##STR00001##

The present invention primarily relates to the use of 3-(4-isobutyl-2-methyl-cyclohexyl)pro-panal, 3-(4-Isobutyl-6-methyl-cyclohexa-1,5-dien-1-yl)propanal, 3-(4-isobutyl-6-meth-ylene-cyclohexen-1-yl)propanal, or 3-(4-isobutyl-6-methyl-cyclohexen-1-yl)propanal as perfuming ingredients. Moreover, the present invention relates to perfume compositions and perfumed products comprising the before mentioned perfuming ingredients. Still more particularly, the invention relates to a method for producing said perfumed products and a method of imparting and/or increasing i) floral and/or ii) green and/or iii) lily of the valley odor characteristics to perfumed products. This invention also relates to 3-(4-isobutyl-2-methyl-cyclohexyl)propanal, 3-(4-Isobutyl-6-methyl-cyclohexa-1,5-dien-1-yl)propanal, 3-(4-isobutyl-6-methylene-cyclohexen-1-yl)propanal, or 3-(4-isobutyl-6-methyl-cyclohexen-yl)propanal and a process for the preparation of said compounds.

The present invention primarily relates to the use of 3-(4-isobutyl-2-methyl-cyclohexyl)pro-panal, 3-(4-Isobutyl-6-methyl-cyclohexa-1,5-dien-1-yl)propanal, 3-(4-isobutyl-6-meth-ylene-cyclohexen-1-yl)propanal, or 3-(4-isobutyl-6-methyl-cyclohexen-1-yl)propanal as perfuming ingredients. Moreover, the present invention relates to perfume compositions and perfumed products comprising the before mentioned perfuming ingredients. Still more particularly, the invention relates to a method for producing said perfumed products and a method of imparting and/or increasing i) floral and/or ii) green and/or iii) lily of the valley odor characteristics to perfumed products. This invention also relates to 3-(4-isobutyl-2-methyl-cyclohexyl)propanal, 3-(4-Isobutyl-6-methyl-cyclohexa-1,5-dien-1-yl)propanal, 3-(4-isobutyl-6-methylene-cyclohexen-1-yl)propanal, or 3-(4-isobutyl-6-methyl-cyclohexen-yl)propanal and a process for the preparation of said compounds.

The present invention relates to the field of perfumery. More particularly, it concerns valuable new chemical intermediates for producing perfuming ingredients. Moreover, the present invention also comprises a process for producing compound of formula (I).

##STR00001##