Abstract: A process for preparing a 2-(1,2,2-trimethyl-3-cyclopentenyl)-2-oxoethyl carboxylate compound of the following general formula (6), wherein R represents a monovalent hydrocarbon group having 1 to 9 carbon atoms, the process comprising esterifying a 2-(1,2,2-trimethyl-3-cyclopentenyl)-2-oxoethyl compound of the following general formula (5), wherein X represents a hydroxyl group or a halogen atom, to form the 2-(1,2,2-trimethyl-3-cyclopentenyl)-2-oxoethyl carboxylate compound (6).

Abstract: The present invention provides a process for preparing (7Z)-7-tricosene of the following formula (3): the process comprising a step of subjecting a nucleophilic reagent, (8Z)-8-pentadecenyl compound of the following general formula (1), wherein M1 represents Li, MgZ1, CuZ1 or CuLiZ1, wherein Z1 represents a halogen atom or an (8Z)-8-pentadecenyl group, to a coupling reaction with a 1-halooctane compound of the following general formula (2), wherein X1 represents a halogen atom, to produce (7Z)-7-tricosene (3).

Abstract: A process for preparing a dienynal compound of the following general formula (2): CH2?CHC?CCH?CH(CH2)nCHO (2), wherein n represents an integer of 0 to 11, the process comprising a step of hydrolyzing a dialkoxyalkadienyne compound of the following general formula (1): CH2?CHC?CCH?CH(CH2)nCH(OR1)(OR2) (1) wherein R1 and R2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, preferably 1 to 8, mere preferably 1 to 4, or R1 and R2 may be bonded to each other to form a divalent hydrocarbon group, R1-R2, having from 2 to 10 carbon atoms, and n represents an integer of 0 to 11, to obtain the dienynal compound (2).

Abstract: A process for preparing 4-penten-2-ynal of the following formula (2): CH2?CHC?CCHO??(2) the process comprising a step of hydrolyzing a 5,5-dialkoxy-1-penten-3-yne compound of the following general formula (1): CH2?CHC?CCH(OR1)(OR2)??(1) wherein R1 and R2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, preferably 1 to 8, more preferably 1 to 4, or R1 and R2 may be bonded to each other to form a divalent hydrocarbon group, R1-R2, having from 2 to 10 carbon atoms, to obtain 4-penten-2-ynal (2).

Abstract: The present invention provides a process for preparing a dimethylcyclobutane compound of the following general formula (1A), the process comprising reacting a dimethylcyclobutanone compound of the following general formula (2) with a phosphonic ester compound of the following general formula (3) to produce an unsaturated ester compound of the following general formula (4), having a dimethylcyclobutane ring, and subjecting the unsaturated ester compound (4), having a dimethylcyclobutane ring, to a reduction reaction to produce the dimethylcyclobutane compound (1A).

Abstract: The present invention provides a process for preparing a diester compound of the following general formula (1), having a dimethylcyclobutane ring, wherein R1 and R2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 10 carbon atoms, the process comprising reacting a dimethylcyclobutanone compound of the following general formula (2), wherein R1 is as defined above, with a phosphonic ester compound of the following general formula (3), wherein R2 and R3 represent, independently of each other, a monovalent hydrocarbon group having 1 to 10 carbon atoms, to produce the diester compound (1), having a dimethylcyclobutane ring.

Abstract: The present invention provides a process for preparing an 11-halo-3-undecene compound (7) in which X1 represents a halogen atom, the process comprising a step of subjecting a nucleophilic reagent, 3-hexenyl compound (5): in which M2 represents Li or MgZ2, wherein Z2 represents a halogen atom or a 3-hexenyl group, to a coupling reaction with a 1-halo-5-halopentane compound (6) in which X3 and X4 may be same with or different from each other and represent a halogen atom, to produce the 11-halo-3-undecene compound (7).

Abstract: The present invention provides a process for preparing 4-methyl-5-nonanone of the following formula (3): the process comprising at least a step of subjecting 2-methylpentanoic anhydride of the following formula (1) and an n-butyl nucleophilic reagent of the following general formula (2) in which M represents Li, MgZ1, or ZnZ1, wherein Z1 represents a halogen atom or an n-butyl group, to a nucleophilic substitution. reaction Coproduce 4-methyl-5-nonanone (3), as well as a process for preparing 4-methyl-5-nonanol of the following formula (5), the process comprising at least steps of preparing 4-methyl-5-nonanone; and subjecting the obtained 4-methyl-5-nonanone and a reducing agent to a reduction reaction to produce 4-methyl-5-nonanol (5).

Abstract: The present invention provides a process for preparing 4-methyl-5-nonanone of the following formula (3), the process comprising at least a step of subjecting pentanoic anhydride of the following formula (1) and a 2-pentyl nucleophilic reagent of the following general formula (2), in which M represents Li, MgZ1, or ZnZ1, wherein Z1 represents a halogen atom or a 2-pentyl group, to a nucleophilic substitution reaction to produce 4-methyl-5-nonanone (3), as well as a process for preparing 4-methyl-5-nonanol of the following formula (7), the process comprising at least steps of preparing 4-methyl-5-nonanone and subjecting the obtained 4-methyl-5-nonanone and a reducing agent to a reduction reaction to produce 4-methyl-5-nonanol (7).

Abstract: The present invention provides a process for preparing (7Z)-7-tricosene of the following formula (3): the process comprising a step of subjecting a nucleophilic reagent, (8Z)-8-pentadecenyl compound of the following general formula (1), wherein M1 represents Li, MgZ1, CuZ1 or CuLiZ1, wherein Z1 represents a halogen atom or an (8Z)-8-pentadecenyl group, to a coupling reaction with a 1-halooctane compound of the following general formula (2), wherein X1 represents a halogen atom, to produce (7Z)-7-tricosene (3).

Abstract: Provided are methods including a method for industrially producing (2S,12Z)-2-acetoxy-12-heptadecene, which is, for example, a sex pheromone of pistachio twig borer. The methods can include a production method comprising a step of reacting racemic (2RS,12Z)-2-hydroxy-12-heptadecene with vinyl benzoate in the presence of a lipase to obtain a mixture of optically active (2R,12Z)-2-benzoyloxy-12-heptadecene of Formula (R,Z-2) and optically active (2S,12Z)-2-hydroxy-12-heptadecene of Formula (S,Z-1), a step of heating the mixture to distill out the optically active (2S,12Z)-2-hydroxy-12-heptadecene (S,Z-1), and a step of acetylating the optically active (2S,12Z)-2-hydroxy-12-heptadecene (S,Z-1) to obtain optically active (2S,12Z)-2-acetoxy-12-heptadecene of Formula (S,Z-3).

Abstract: The object of the present invention is to provide a process for preparing a 5-alken-1-yne compound efficiently at low costs and a process for preparing (2E,6Z)-2,6-nonadienal by making use of the aforesaid process for preparing the 5-alken-1-yne compound. There is provided a process for preparing a 5-alken-1-yne compound of the following formula (4): Y—Z—CR1?CR2—(CH2)2—C?CH (4) in which Y in formula (4) represents a hydrogen atom or a hydroxyl group, the process comprising at least steps of: subjecting (i) an alkenylmagnesium halide compound prepared from a haloalkene compound of the following formula (1): Y—Z—CR1?CR2—(CH2)2—X1 (1) and (ii) an alkyne compound of the following formula (2): X2—C?C—Si(R3)(R4)(R5) (2) to a coupling reaction to form a silane compound of the following formula (3): Y—Z—CR1?CR2—(CH2)2—C?C—Si(R3)(R4)(R5) (3); and subjecting the silane compound (3) to a desilylation reaction to form the 5-alken-1-yne compound (4).

Abstract: The object of the present invention is to provide an industrial and economical process for preparing (E2)-cis-6,7-epoxy-2-nonenal of the following formula (3): The present invention provides a process for preparing (E2)-cis-6,7-epoxy-2-nonenal (3), comprising at least steps of: subjecting (Z3,Z6)-3,6-nonadien-1-ol of the following formula (1) to oxidation: to form (E2,Z6)-2,6-nonadienal of the following formula (2); and epoxidizing the resulting (E2,Z6)-2,6-nonadienal to form the aforesaid (E2)-cis-6,7-epoxy-2-nonenal (3).

Abstract: A process to prepare (9E,11Z)-9,11-hexadecadienyl acetate with a good yield and high purity of the general formula (1): CH3—(CH2)3—CH?CH—CH?CH—(CH2)a—X.=The process includes a step of conducting a Wittig reaction between a haloalkenal of the general formula (2): OHC—CH?CH—(CH2)a—X, and a triarylphosphonium pentylide of the general formula (3): CH3—(CH2)3—CH?—P+Ar3, to obtain the 1-haloalkadiene, and the use of a (7E,9Z)-1-halo-7,9-tetradecadiene obtained by the process for a process of preparing (9E, 11Z)-9,11-hexadecadienyl acetate.

Abstract: A composition containing a substance having sex pheromone activity on San Jose scale (SJS) after finding the substance. More specifically, there are provided a composition having sex pheromone activity on SJS, the composition containing 3,7-dimethyl-7-octenyl propionate as a substance having sex pheromone activity on SJS; an attractant for SJS, the attractant containing the composition and a support for supporting the composition in such a manner as to allow the substance to be released; a mating disruptant for SJS, the disruptant containing the composition and a container for storing the composition in such a manner as to allow the substance to be released; and a method for attracting SJS or disrupting mating of SJS, the method including a step of installing the attractant or the mating disruptant for SJS in a field to release the substance from the attractant or the mating disruptant into the field.

Abstract: The object of the present invention is to provide an industrial and economical process for preparing (E2,Z6)-2,6-nonadienal of the following formula (4): The present invention provides a process for preparing (E2,Z6)-2,6-nonadienal (4), comprising at least steps of: subjecting (Z3,Z6)-3,6-nonadien-1-ol of the following formula (1): to oxidation with a sulfoxide compound of the following formula (2): CH3(R1)S?O??(2) in which R1 represents a monovalent hydrocarbon group having from 1 to 12 carbon atoms, in the presence of a sulfur trioxide complex and an amine compound of the following formula (3): N(R2)(R3)(R4)??(3) in which R2, R3, and R4 each independently represent a monovalent hydrocarbon group having from 1 to 12 carbon atoms, or R3 and R4 may be bonded to each other to form a divalent hydrocarbon group having from 3 to 12 carbon atoms, R3-R4, to form the aforesaid (E2,Z6)-2,6-nonadienal (4).

Abstract: The present invention provides a process for preparing 4-methyl-5-nonanone of the following formula (3), the process comprising at least a step of subjecting pentanoic anhydride of the following formula (1) and a 2-pentyl nucleophilic reagent of the following general formula (2), in which M represents Li, MgZ1, or ZnZ1, wherein Z1 represents a halogen atom or a 2-pentyl group, to a nucleophilic substitution reaction to produce 4-methyl-5-nonanone (3), as well as a process for preparing 4-methyl-5-nonanol of the following formula (7), the process comprising at least steps of preparing 4-methyl-5-nonanone and subjecting the obtained 4-methyl-5-nonanone and a reducing agent to a reduction reaction to produce 4-methyl-5-nonanol (7).

Abstract: The present invention provides a process for preparing 4-methyl-5-nonanone of the following formula (3): the process comprising at least a step of subjecting 2-methylpentanoic anhydride of the following formula (1) and an n-butyl nucleophilic reagent of the following general formula (2) in which M represents Li, MgZ1, or ZnZ1, wherein Z1 represents a halogen atom or an n-butyl group, to a nucleophilic substitution. reaction Coproduce 4-methyl-5-nonanone (3), as well as a process for preparing 4-methyl-5-nonanol of the following formula (5), the process comprising at least steps of preparing 4-methyl-5-nonanone; and subjecting the obtained 4-methyl-5-nonanone and a reducing agent to a reduction reaction to produce 4-methyl-5-nonanol (5).

Abstract: 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).

Abstract: A halide compound having one or more carbon-carbon unsaturated bonds is catalytically reduced with substantially no dehalogenation to produce a reduced halide compound in which at least one of the one or more unsaturated bonds is reduced. Specifically provided is a method for producing a reduced halide compound including steps of: reacting a nickel compound, a zinc compound, and a borohydride compound in a solvent to obtain a reduction catalyst; and subjecting a halide compound having one or more carbon-carbon unsaturated bonds to catalytic reduction in the presence of the reduction catalyst to reduce at least one of the one or more carbon-carbon unsaturated bonds to thereby obtain a reduced halide compound.