Abstract: Provided herein are convenient and efficient processes for preparing (2E,6Z)-2,6-nonadienal and (2E)-6,7-epoxy-2-nonenal with a reduced number of steps. For instance, provided herein is a process for preparing (2E,6Z)-2,6-nonadienal, including at least steps of subjecting a (6,6-dialkoxy-4-hexenylidene)triarylphosphorane compound of the general formula: Ar3P?CH(CH2)2CH?CHCH(OR1)(OR2) to a Witting reaction with propanal to form a 1,1-dialkoxy-(6Z)-2,6-nonadiene compound of the general formula (6); and subjecting the 1,1-dialkoxy-(6Z)-2,6-nonadiene compound to hydrolysis to form (2E,6Z)-2,6-nonadienal. Also provided is a process for preparing (2E)-cis-6,7-epoxy-2-nonenal of the formula (8), comprising a step of subjecting (2E,6Z)-2,6-nonadienal thus obtained to epoxidation to form (2E)-cis-6,7-epoxy-2-nonenal.

Abstract: An efficient process for preparing (9E,11Z)-9,11-hexadecadienal of formula (4) is provided. The process includes at least steps of: conducting a nucleophilic substitution reaction between an (8E,10Z)-8,10-pentadecadienyl magnesium halide derived from an (8E,10Z)-1-halo-8,10-pentadecadiene of (1): and an orthoformate ester (2) to thereby prepare a (9E, 11Z)-1,1-dialkoxy-9, 11-hexadecadiene (3): and hydrolyzing the (9E, 11Z)-1,1-dialkoxy-9,11-hexadecadiene (3) to obtain (9E, 11Z)-9,11-hexadecadienal (4).

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(R?)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 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: 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: Provided herein are convenient and efficient processes for preparing (2E,6Z)-2,6-nonadienal and (2E)-6,7-epoxy-2-nonenal with a reduced number of steps. For instance, provided herein is a process for preparing (2E,6Z)-2,6-nonadienal, including at least steps of subjecting a (6,6-dialkoxy-4-hexenylidene)triarylphosphorane compound of the general formula: Ar3P?CH(CH2)2CH?CHCH(OR1)(OR2) to a Witting reaction with propanal to form a 1,1-dialkoxy-(6Z)-2,6-nonadiene compound of the general formula (6); and subjecting the 1,1-dialkoxy-(6Z)-2,6-nonadiene compound to hydrolysis to form (2E,6Z)-2,6-nonadienal. Also provided is a process for preparing (2E)-cis-6,7-epoxy-2-nonenal of the formula (8), comprising a step of subjecting (2E,6Z)-2,6-nonadienal thus obtained to epoxidation to form (2E)-cis-6,7-epoxy-2-nonenal.

Abstract: An efficient process for preparing (9E,11Z)-9,11-hexadecadienal of formula (4) is provided. The process includes at least steps of: conducting a nucleophilic substitution reaction between an (8E,10Z)-8,10-pentadecadienyl magnesium halide derived from an (8E,10Z)-1-halo-8,10-pentadecadiene of (1): and an orthoformate ester (2) to thereby prepare a (9E, 11Z)-1,1-dialkoxy-9, 11-hexadecadiene (3): and hydrolyzing the (9E, 11Z)-1,1-dialkoxy-9,11-hexadecadiene (3) to obtain (9E, 11Z)-9,11-hexadecadienal (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.

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: One object of the invention is to provide a method for preparing a 9,9-dialkoxy-7-nonynoate ester and (7E)-7,9-decadienoate ester, which are valuable as intermediates. The method for preparing a (7E)-7,9-decadienoate ester (5) comprises at least steps of: hydrolyzing a 9,9-dialkoxy-7-nonenoate ester (2), R3O(R2O)CHCH?CH(CH2)5CO2R1, to form a (7E)-9-oxo-7-nonenoate ester (3); and subjecting the (7E)-9-oxo-7-nonenoate ester (3) to a Wittig reaction with a triarylphosphonium methylide (4), Ar3P?CH2, to form the (7E)-7,9-decadienoate ester (5). The 9,9-dialkoxy-7-nonenoate ester may be prepared by, for example, reducing a 9,9-dialkoxy-7-nonynoate ester (1).

Abstract: One object of the invention is to provide a method for preparing a 9,9-dialkoxy-7-nonynoate ester and (7E)-7,9-decadienoate ester, which are valuable as intermediates. The method for preparing a (7E)-7,9-decadienoate ester (5) comprises at least steps of: hydrolyzing a 9,9-dialkoxy-7-nonenoate ester (2), R3O(R2O)CHCH?CH(CH2)5CO2R1, to form a (7E)-9-oxo-7-nonenoate ester (3); and subjecting the (7E)-9-oxo-7-nonenoate ester (3) to a Wittig reaction with a triarylphosphonium methylide (4), Ar3P?CH2, to form the (7E)-7,9-decadienoate ester (5). The 9,9-dialkoxy-7-nonenoate ester may be prepared by, for example, reducing a 9,9-dialkoxy-7-nonynoate ester (1).

Abstract: A high-yield process for preparing (4Z,7Z)-4,7-decadien-1-yl acetate, with reduced number of steps, without using a protecting group. A process for preparing (4Z,7Z)-4,7-decadien-1-yl acetate is provided, the process including at least the following steps: reducing a 10-halo-3,6-decadiyne of the general formula (1) to form a (3Z,6Z)-10-halo-3,6-decadiene of the general formula (2); and converting the (3Z,6Z)-10-halo-3,6-decadiene into (4Z,7Z)-4,7-decadien-1-yl acetate of the formula (4) having an acetoxy group in place of the halogen atom of the (3Z,6Z)-10-halo-3,6-decadiene.

Abstract: A high-yield process for preparing (4Z,7Z)-4,7-decadien-1-yl acetate, with reduced number of steps, without using a protecting group. A process for preparing (4Z,7Z)-4,7-decadien-1-yl acetate is provided, the process including at least the following steps: reducing a 10-halo-3,6-decadiyne of the general formula (1) to form a (3Z,6Z)-10-halo-3,6-decadiene of the general formula (2); and converting the (3Z,6Z)-10-halo-3,6-decadiene into (4Z,7Z)-4,7-decadien-1-yl acetate of the formula (4) having an acetoxy group in place of the halogen atom of the (3Z,6Z)-10-halo-3,6-decadiene.

Abstract: Methods of producing a 2,4-dienal acetal compound and a 2,4-dienal compound useful as synthesis intermediates of a sex pheromone compound having a conjugated diene structure or a conjugated triene structure. More specifically, a method produces a 2,4-dienal acetal compound of Formula (2): R1CH?CH—CH?CH—CH(OR2)(OR3), including a step of subjecting a 2-enal acetal compound having a leaving group X at position C5 and being expressed by Formula (1): R1CHX—CH2—CH?CH—CH(OR2)(OR3) to an elimination reaction in the presence of a base to obtain the 2,4-dienal acetal compound (2); and a method for producing a 2,4-dienal compound of Formula (3): R1CH?CH—CH?CH—CHO, further including a step of deprotecting the 2,4-dienal acetal compound (2) to obtain the 2,4-dienal compound (3).

Abstract: Provided are a 1-halo-6,9-pentadecadiene useful as an intermediate having a skipped diene skeleton and a method for producing (7Z,10Z)-7,10-hexadecadienal. More specifically, provided are a method for producing (7Z,10Z)-7,10-hexadecadienal including steps of subjecting a Grignard reagent formed from a (6Z,9Z)-1-halo-6,9-pentadecadiene to a nucleophilic substitution reaction with an orthoformate ester to obtain a (7Z,10Z)-1,1-dialkoxy-7,10-hexadecadiene; and hydrolyzing the (7Z,10Z)-1,1-dialkoxy-7,10-hexadecadiene in the absence of an oxidation reaction to obtain the (7Z,10Z)-7,10-hexadecadienal; and the like.

Abstract: Methods of producing a 2,4-dienal acetal compound and a 2,4-dienal compound useful as synthesis intermediates of a sex pheromone compound having a conjugated diene structure or a conjugated triene structure. More specifically, a method produces a 2,4-dienal acetal compound of Formula (2): R1CH?CH—CH?CH—CH(OR2)(OR3), including a step of subjecting a 2-enal acetal compound having a leaving group X at position C5 and being expressed by Formula (1): R1CHX—CH2—CH?CH—CH(OR2)(OR3) to an elimination reaction in the presence of a base to obtain the 2,4-dienal acetal compound (2); and a method for producing a 2,4-dienal compound of Formula (3): R1CH?CH—CH?CH—CHO, further including a step of deprotecting the 2,4-dienal acetal compound (2) to obtain the 2,4-dienal compound (3).

Abstract: Provided are a 1-halo-6,9-pentadecadiene useful as an intermediate having a skipped diene skeleton and a method for producing (7Z,10Z)-7,10-hexadecadienal. More specifically, provided are a method for producing (7Z,10Z)-7,10-hexadecadienal including steps of subjecting a Grignard reagent formed from a (6Z,9Z)-1-halo-6,9-pentadecadiene to a nucleophilic substitution reaction with an orthoformate ester to obtain a (7Z,10Z)-1,1-dialkoxy-7,10-hexadecadiene; and hydrolyzing the (7Z,10Z)-1,1-dialkoxy-7,10-hexadecadiene in the absence of an oxidation reaction to obtain the (7Z,10Z)-7,10-hexadecadienal; and the like.

Abstract: Provided are a method for producing a terminal conjugated dienal compound without an oxidation reaction and a terminal hydroxyacetal compound useful as an intermediate in the method. More specifically, provided are a method for producing an (E)-dienal compound comprising the steps of: a metalation reaction of an alkynal acetal compound (1) to obtain an organic metal compound (2), an addition reaction of (2) to ethylene oxide to obtain a hydroxyalkynal acetal compound (3), a reduction reaction of (3) to obtain an (E)-hydroxyalkenal acetal compound (4), a functional group conversion reaction of (4) to obtain an (E)-alkenal acetal compound (5) having a leaving group X, an elimination reaction of (5) to obtain an (E)-dienal acetal compound (6), and a hydrolysis reaction of (6) to obtain the (E)-dienal compound (7); and others.

Abstract: There is provided a method for producing ethyl 4-methyloctanoate at a lower cost, by fewer steps, and in higher yield. More specifically, there is provided a method for producing ethyl 4-methyloctanoate comprising the steps of: reacting 1-chloro-2-methylhexane through malonic ester synthesis to obtain diethyl 2-methylhexylmalonate, and subjecting the diethyl 2-methylhexylmalonate to a Krapcho reaction to obtain ethyl 4-methyloctanoate.

Abstract: Provided are a method for efficiently producing an asymmetric conjugated diyne from an inexpensive and safe alternative compound to hydroxylamine hydrochloride and a method for producing a Z,Z-conjugated diene compound from the asymmetric conjugated diyne compound thus obtained. More specifically, provided is a method for producing an asymmetric conjugated diyne compound comprising a step of subjecting a terminal alkyne compound (1): HC?C—Z1—Y1 to a coupling reaction with an alkynyl halide (2): Y2—Z2—C?C—X by using sodium borohydride in water and an organic solvent in the presence of a copper catalyst and a base to obtain the asymmetric conjugated diyne compound (3): Y2—Z2—C?C—C?C—Z1—Y1. In addition, provided is a method for producing a Z,Z-conjugated diene compound by reducing the resulting asymmetric conjugated diyne compound, or the like.