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).

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Provided is a method with which an α-allylated cycloalkanone is obtained from a macroyclic compound used as a starting material. The method is a method for producing an α-allylated cycloalkanone represented by General Formula (IV), and the method includes a step of reacting a compound represented by General Formula (I) and/or a compound represented by General Formula (II) with a compound represented by General Formula (III) in the presence of an acid catalyst to produce an α-allylated cycloalkanone represented by General Formula (IV), the acid catalyst including an acid catalyst that includes an ammonium cation and an anion.

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where R.sup.1, R.sup.2, and R.sup.3 are the same or different and each of them is an alky group having 1 or mom and 4 or less of carbon atoms, the group -A.sup.1- (it should be noted that the front bond refers to a bond that binds to the carbon atom C.sup.1 and the back bond refers to a bond that binds to the carbon atom C.sup.2) is an alkylene group having 4 or more and 20 or les of carbon atoms that optionally contains a hetero atom and optionally has a substituent, and R.sup.4 is a hydrogen atom or an alkyl group having 1 or more and 4 or less of carbon atoms.

Provided is a method with which an α-allylated cycloalkanone is obtained from a macroyclic compound used as a starting material. The method is a method for producing an α-allylated cycloalkanone represented by General Formula (IV), and the method includes a step of reacting a compound represented by General Formula (I) and/or a compound represented by General Formula (II) with a compound represented by General Formula (III) in the presence of an acid catalyst to produce an α-allylated cycloalkanone represented by General Formula (IV), the acid catalyst including an acid catalyst that includes an ammonium cation and an anion.

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where R.sup.1, R.sup.2, and R.sup.3 are the same or different and each of them is an alky group having 1 or mom and 4 or less of carbon atoms, the group -A.sup.1- (it should be noted that the front bond refers to a bond that binds to the carbon atom C.sup.1 and the back bond refers to a bond that binds to the carbon atom C.sup.2) is an alkylene group having 4 or more and 20 or les of carbon atoms that optionally contains a hetero atom and optionally has a substituent, and R.sup.4 is a hydrogen atom or an alkyl group having 1 or more and 4 or less of carbon atoms.

Provided is a method with which an α-allylated cycloalkanone is obtained from a cyclic compound cycloalkanone used as a starting material. The method is a method for producing an α-allylated cycloalkanone represented by General Formula (III), and the method includes: a step 1: reacting a compound represented by General Formula (I) and alcohol having 1 or more and 4 or less of carbon atoms in the presence of a first acid catalyst and optionally a dehydrating agent; and a step 2: reacting a crude product obtained in the step 1 and a compound represented by General Formula (II) in the presence of a second acid catalyst to produce an α-allylated cycloalkanone represented by General Formula (III). The step 1 and the step 2 are consecutively performed. In the formulae above, the group -A.sup.1- (it should be noted that the front bond refers to a bond that binds to the carbon atom C.sup.1 and the back bond refers to a bond that binds to the carbon atom C.sup.2) is an alkylene group having 4 or more and 20 or less of carbon atoms that optionally contains a hetero atom and optionally has a substituent, and R.sup.4 is a hydrogen atom or an alkyl group having 1 or more and 4 or less of carbon atoms.

Provided is a method with which an α-allylated cycloalkanone is obtained from a cyclic compound cycloalkanone used as a starting material. The method is a method for producing an α-allylated cycloalkanone represented by General Formula (III), and the method includes: a step 1: reacting a compound represented by General Formula (I) and alcohol having 1 or more and 4 or less of carbon atoms in the presence of a first acid catalyst and optionally a dehydrating agent; and a step 2: reacting a crude product obtained in the step 1 and a compound represented by General Formula (II) in the presence of a second acid catalyst to produce an α-allylated cycloalkanone represented by General Formula (III). The step 1 and the step 2 are consecutively performed. In the formulae above, the group -A.sup.1- (it should be noted that the front bond refers to a bond that binds to the carbon atom C.sup.1 and the back bond refers to a bond that binds to the carbon atom C.sup.2) is an alkylene group having 4 or more and 20 or less of carbon atoms that optionally contains a hetero atom and optionally has a substituent, and R.sup.4 is a hydrogen atom or an alkyl group having 1 or more and 4 or less of carbon atoms.

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##

Provided is a method with which an α-allylated cycloalkanone is obtained from a cyclic compound cycloalkanone used as a starting material. The method is a method for producing an α-allylated cycloalkanone represented by General Formula (III), and the method includes: a step 1: reacting a compound represented by General Formula (I) and alcohol having 1 or more and 4 or less of carbon atoms in the presence of a first acid catalyst and optionally a dehydrating agent; and a step 2: reacting a crude product obtained in the step 1 and a compound represented by General Formula (II) in the presence of a second acid catalyst to produce an α-allylated cycloalkanone represented by General Formula (III). The step 1 and the step 2 are consecutively performed. In the formulae above, the group -A.sup.1- (it should be noted that the front bond refers to a bond that binds to the carbon atom C.sup.1 and the back bond refers to a bond that binds to the carbon atom C.sup.2) is an alkylene group having 4 or more and 20 or less of carbon atoms that optionally contains a hetero atom and optionally has a substituent, and R.sup.4 is a hydrogen atom or an alkyl group having 1 or more and 4 or less of carbon atoms.

Provided is a method with which an α-allylated cycloalkanone is obtained from a cyclic compound cycloalkanone used as a starting material. The method is a method for producing an α-allylated cycloalkanone represented by General Formula (III), and the method includes: a step 1: reacting a compound represented by General Formula (I) and alcohol having 1 or more and 4 or less of carbon atoms in the presence of a first acid catalyst and optionally a dehydrating agent; and a step 2: reacting a crude product obtained in the step 1 and a compound represented by General Formula (II) in the presence of a second acid catalyst to produce an α-allylated cycloalkanone represented by General Formula (III). The step 1 and the step 2 are consecutively performed. In the formulae above, the group -A.sup.1- (it should be noted that the front bond refers to a bond that binds to the carbon atom C.sup.1 and the back bond refers to a bond that binds to the carbon atom C.sup.2) is an alkylene group having 4 or more and 20 or less of carbon atoms that optionally contains a hetero atom and optionally has a substituent, and R.sup.4 is a hydrogen atom or an alkyl group having 1 or more and 4 or less of carbon atoms.

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 (4), the method including the steps of: hydrolyzing a 7-methyl-3-methylene-7-octenal acetal compound (1) to obtain 7-methyl-3-methylene-7-octenal (2); reducing the 7-methyl-3-methylene-7-octenal (2) to obtain 7-methyl-3-methylene-7-octenol (3); and esterifying the 7-methyl-3-methylene-7-octenol (3) to obtain a 7-methyl-3-methylene-7-octenyl carboxylate compound (4). ##STR00001##