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: The present invention provides a process for preparing an alkoxymethyl alkynyl ether compound having a terminal triple bond of the following formula (4): H—C?C(CH2)aOCH2OCH2R (4), wherein R represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, and “a” represents an integer of 1 to 10, the method comprising subjecting an alkynol compound having a terminal triple bond of the following formula (1): H—C?C(CH2)aOH (1), wherein “a” is as defined above, to an alkoxymethylation with a halomethyl alkyl ether compound of the following formula (3): RCH2OCH2X (3), wherein X represents a halogen atom, and R is as defined above, in the presence of a dialkylaniline compound of the following formula (2): [CH3(CH2)b][CH3(CH2)c]NC6H5 (2), wherein b and c represent, independently of each other, an integer of 0 to 9, to form the alkoxymethyl alkynyl ether compound (4) having a terminal triple bond.

Abstract: The present invention provides processes for preparing an ?-necrodyl compound of the following general formula (3): wherein R2 represents a monovalent hydrocarbon group having 1 to 9 carbon atoms, the process comprising: subjecting a 3, 5, 5-trimethyl-3-cyclopentene compound of the following general formula (1): wherein R2 is as defined above, and X represents a leaving group, to a nucleophilic substitution reaction with a methylating agent of the following general formula (2): wherein M represents Li, MgZ1, ZnZ1, Cu, CuZ1, or CuLiZ1, and Z1 represents a halogen atom or a methyl group, to form the ?-necrodyl compound (3). The present invention further provides processes for preparing ?-necrodyl compounds of the following general formula (4): wherein R2 represents a monovalent hydrocarbon group having 1 to 9 carbon atoms, the process comprising: subjecting the ?-necrodyl compound (3) thus obtained to a positional isomerization reaction at the double bond to form the ?-necrodyl compound (4).

Abstract: The present invention relates to a process for preparing a 3-isopropenyl-6-heptenal compound of the following formula (2): wherein R1 represents a hydrogen atom or a methyl group, the process comprising: subjecting a 3-isopropenyl-6-heptenoate ester compound of the following formula (1): wherein R1 is as defined above, and R2 represents a monovalent hydrocarbon group having 1 to 10 carbon atoms, to a reduction reaction with a reducing agent to form the 3-isopropenyl-6-heptenal compound (2).

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 (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 R1 and R2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R1 and R2 may form together a divalent hydrocarbon group, R1—R2, 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 R1 and R2 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).

Abstract: The present invention relates to a haloalkenyl alkoxymethyl ether compound of the following general formula (1): R1CH2OCH2OCH2CH2CH?CH(CH2)aX1 (1) wherein R1 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, X1 represents a halogen atom, and “a” represents an integer of 3 to 14. The present invention also relates to processes for preparing a terminal conjugated alkadien-1-yl acetate compound of the following general formula (5): CH2?CHCH?CH(CH2)aOAc (5) wherein “a” is as defined above, and Ac represents an acetyl group, and a terminal conjugated alkadien-1-ol compound of the following general formula (6): CH2?CHCH?CH(CH2)aOH (6) wherein “a” is as defined above, from the haloalkenyl alkoxymethyl ether compound (1).

Abstract: The present invention provides a process for preparing a terminal conjugated alkadienal compound of the following general formula (5): CH2?CHCH?CH(CH2)aCHO ??(5) wherein “a” represents an integer of 1 to 15, from a dialkoxyalkenyl alkoxymethyl ether compound of the following general formula (1): R1CH2OCH2OCH2CH2CH?CH(CH2)aCH(OR2)(OR3) ??(1) wherein R1 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, R2 and R3 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R2 and R3 may form together a divalent hydrocarbon group, R2-R3, having 2 to 10 carbon atoms, and “a” is as defined above.

Abstract: The present invention relates to a 6-hydroxy-3-hexenyl alkoxymethyl ether compound of the following general formula (1): HOCH2CH2CH?CHCH2CH2OCH2OCH2R? (1), R1 representing a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group; and also relates to a process for preparing a 3,13-octadecadien-1-ol compound of the following formula (6): CH3(CH2)3CH?CH(CH2)8CH?CHCH2CH2OH (6) from the 6-hydroxy-3-hexenyl alkoxymethyl ether compound (1).

Abstract: The present invention provides a process for preparing 2-isopropenyl-5-methyl-4-hexenoic acid of the following formula (4), comprising steps of: subjecting a Grignard reagent of the following general formula (1), wherein R1 represents a linear, branched, or aromatic monovalent hydrocarbon group having 1 to 8 carbon atoms, and X represents a chlorine atom, a bromine atom, or an iodine atom, and 1,1,1,3,3,3-hexamethyldisilazane to a deprotonation reaction to form a 1,1,1,3,3,3-hexamethyldisilazane derivative; and subjecting 2-methyl-3-buten-2-yl 3-methyl-2-butenoate of the following formula (3) to a rearrangement reaction in the presence of the 1,1,1,3,3,3-hexamethyldisilazane derivative to form 2-isopropenyl-5-methyl-4-hexenoic acid (4).

Abstract: The present invention provides a process for preparing a compound of the following general formula (2): wherein R1 represents a monovalent hydrocarbon group having 1 to 10 carbon atoms, and R3 represents a hydrogen atom or a methyl group, the process comprising: subjecting a compound of the following general formula (1): wherein R1 and R2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 10 carbon atoms, R3 represents a hydrogen atom or a methyl group, and the wavy bond represents an E-configuration, a Z-configuration, or a mixture thereof, to a Dieckmann condensation in the presence of base to form the compound (2).

Abstract: The present invention provides processes for preparing an ?-necrodyl compound of the following general formula (3): wherein R2 represents a monovalent hydrocarbon group having 1 to 9 carbon atoms, the process comprising: subjecting a 3, 5, 5-trimethyl-3-cyclopentene compound of the following general formula (1): wherein R2 is as defined above, and X represents a leaving group, to a nucleophilic substitution reaction with a methylating agent of the following general formula (2): wherein M represents Li, MgZ1, ZnZ1, Cu, CuZ1, or CuLiZ1, and Z1 represents a halogen atom or a methyl group, to form the ?-necrodyl compound (3). The present invention further provides processes for preparing ?-necrodyl compounds of the following general formula (4): wherein R2 represents a monovalent hydrocarbon group having 1 to 9 carbon atoms, the process comprising: subjecting the ?-necrodyl compound (3) thus obtained to a positional isomerization reaction at the double bond to form the ?-necrodyl compound (4).

Abstract: The present invention provides a process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate (5): wherein Ac represents an acetyl group, the process comprising steps of: subjecting a 2-methyl-2,6-heptadiene compound (1) having a leaving group X at position 1: wherein X represents an acyloxy group having 1 to 10 carbon atoms including the carbon atom of the carbonyl group, an alkanesulfonyloxy group having 1 to 10 carbon atoms, an arenesulfonyloxy group having 6 to 20 carbon atoms, or a halogen atom, to a nucleophilic substitution reaction with a 3-methylpentyl nucleophilic reagent (2) having a protected hydroxyl group at position 5: wherein M represents Li, MgZ1, ZnZ1, Cu, CuZ1, or CuLiZ1, wherein Z1 represents a halogen atom or a CH2CH2CH(CH3)CH2CH2OR group, and R represents a protecting group for a hydroxyl group, to form a 6-isopropenyl-3-methyl-9-decene compound (3) having a protected hydroxyl group at position 1: wherein R is as defined above; subjecting the 6-isopropenyl-3-methyl-9-decene compound (3

Abstract: 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 R1 and R2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R1 and R2 may form together a divalent hydrocarbon group, R1-R2, 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 R1 and R2 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).

Abstract: A composition for forming an aerosol, an aerosol sprayer for insect pest mating disruption, and a method for insect pest mating disruption, thereby reducing disadvantageous effects caused by falling to a ground surface and oxidative decomposition of the sprayed particles. More specifically, the composition including an aerosol stock solution containing an aliphatic linear aldehyde having 10 to 20 carbon atoms and a non-alcoholic diluent, and a propellant, wherein a weight ratio of the aerosol stock solution to the propellant is from 45:55 to 65:35; the sprayer including the composition and a pressure resistant container for enclosing the composition therein, wherein sprayed particles at a spray travel distance of 15 cm have a median particle size (Dv50) at 25° C. of from 35 to 65 ?m by a volume-based cumulative particle size distribution and; the method using the aerosol sprayer; and the like.

Abstract: 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 M1 represents Li, MgZ1, ZnZ1, Cu, CuZ1, or CuLiZ1, wherein Z1 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 X1 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).

Abstract: The present invention provides a process for preparing 2-isopropenyl-5-methyl-4-hexenoic acid of the following formula (4), comprising steps of: subjecting a Grignard reagent of the following general formula (1), wherein R1 represents a linear, branched, or aromatic monovalent hydrocarbon group having 1 to 8 carbon atoms, and X represents a chlorine atom, a bromine atom, or an iodine atom, and 1,1,1,3,3,3-hexamethyldisilazane to a deprotonation reaction to form a 1,1,1,3,3,3-hexamethyldisilazane derivative; and subjecting 2-methyl-3-buten-2-yl 3-methyl-2-butenoate of the following formula (3) to a rearrangement reaction in the presence of the 1, 1, 1,3,3,3-hexamethyldisilazane derivative to form 2-isopropenyl-5-methyl-4-hexenoic acid (4).

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, 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, and n represents an integer of 0 to 11, to obtain the dienynal compound (2).

Abstract: The present invention provide for preparing a formylalkenyl alkoxymethyl ether compound of the following general formula (2): R3CH2OCH2O(CH2)aCH?CHCHO (2), wherein R3 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group; and “a” represents an integer of 1 to 10, the process comprising: hydrolyzing a dialkoxyalkenyl alkoxymethyl ether compound of the following general formula (1): R3CH2OCH2O(CH2)aCH?CHCH(OR1)(OR2) (1), wherein R1 and R2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R1 and R2 may form together a divalent hydrocarbon group, R1-R2, having 2 to 10 carbon atoms; and R3 and “a” are as defined above, in the presence of an acid while removing an alcohol compound thus generated to form the formylalkenyl alkoxymethyl ether 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).