An industrially excellent production method for cycloalkyl(trifluoromethyl)benzene is free of complicated steps, small in the number of steps, and high in production efficiency. Cycloalkyl(trifluoromethyl)benzene is produced by reacting a halogen-substituted trifluoromethyl benzene with magnesium metal to produce a Grignard reagent and cross-coupling the Grignard reagent with a cycloalkyl halide in the presence of an iron salt or a cobalt salt at a reaction temperature of 60 C. to 80 C.

An industrially excellent production method for cycloalkyl(trifluoromethyl)benzene is free of complicated steps, small in the number of steps, and high in production efficiency. Cycloalkyl(trifluoromethyl)benzene is produced by reacting a halogen-substituted trifluoromethyl benzene with magnesium metal to produce a Grignard reagent and cross-coupling the Grignard reagent with a cycloalkyl halide in the presence of an iron salt or a cobalt salt at a reaction temperature of 60 C. to 80 C.

The present invention provides a process for preparing an 11-halo-3-undecene compound (7) in which X.sup.1 represents a halogen atom, the process comprising a step of subjecting a nucleophilic reagent, 3-hexenyl compound (5): in which M.sup.2 represents Li or MgZ.sup.2, wherein Z.sup.2 represents a halogen atom or a 3-hexenyl group, to a coupling reaction with a 1-halo-5-halopentane compound (6) in which X.sup.3 and X.sup.4 may be same with or different from each other and represent a halogen atom, to produce the 11-halo-3-undecene compound (7). The present invention also provides a process for preparing a 9-dodecenal compound (4): the process comprising a step of subjecting a nucleophilic reagent, 8-undecenyl compound (1) in which M.sup.1 represents Li or MgZ.sup.1, wherein Z.sup.1 represents a halogen atom or an 8-undecenyl group, and an orthoformic ester compound (2) in which R may be same with or different from each other and represents an alkyl group having 1 to 6 carbon atoms, to a nucleophilic substitution reaction to produce a 1,1-dialkoxy-9-dodecene compound (3) in which R are as defined above; and hydrolyzing the 1,1-dialkoxy-9-dodecene compound (3) thus obtained to produce the 9-dodecenal compound (4).

##STR00001##

The present invention provides a process for preparing an 11-halo-3-undecene compound (7) in which X.sup.1 represents a halogen atom, the process comprising a step of subjecting a nucleophilic reagent, 3-hexenyl compound (5): in which M.sup.2 represents Li or MgZ.sup.2, wherein Z.sup.2 represents a halogen atom or a 3-hexenyl group, to a coupling reaction with a 1-halo-5-halopentane compound (6) in which X.sup.3 and X.sup.4 may be same with or different from each other and represent a halogen atom, to produce the 11-halo-3-undecene compound (7). The present invention also provides a process for preparing a 9-dodecenal compound (4): the process comprising a step of subjecting a nucleophilic reagent, 8-undecenyl compound (1) in which M.sup.1 represents Li or MgZ.sup.1, wherein Z.sup.1 represents a halogen atom or an 8-undecenyl group, and an orthoformic ester compound (2) in which R may be same with or different from each other and represents an alkyl group having 1 to 6 carbon atoms, to a nucleophilic substitution reaction to produce a 1,1-dialkoxy-9-dodecene compound (3) in which R are as defined above; and hydrolyzing the 1,1-dialkoxy-9-dodecene compound (3) thus obtained to produce the 9-dodecenal compound (4).

##STR00001##

The present invention provides a method for preparing a compound of formula (I) F(CF.sub.2).sub.n(CH.sub.2).sub.mR.sub.o (I), wherein n is an integer from 2 to 12, m is an integer from 0 to 7, R.sub.o is a linear or branched saturated alkyl group and o depicts the number of carbon atoms, o is an integer from 1 to 12, and wherein m+o is an integer from 2 to 12; comprising reacting a fluorinated compound of formula (II) F(CF.sub.2).sub.n(CH.sub.2).sub.mX (II), wherein X is Cl, Br, I, MgCl, MgBr, or MgI, and n and m have the same meaning as in formula (I), with a non-fluorinated compound of formula (III) R.sub.oY (III), wherein Y is Cl, Br, I, MgCl, MgBr, or MgI, with the proviso that when X is Cl, Br or I, Y is MgCl, MgBr or MgI, and when X is MgCl, MgBr or MgI, Y is Cl, Br or I, and R.sub.o has the same meaning as in formula (I).

The present invention provides a method for preparing a compound of formula (I) F(CF.sub.2).sub.n(CH.sub.2).sub.mR.sub.o (I), wherein n is an integer from 2 to 12, m is an integer from 0 to 7, R.sub.o is a linear or branched saturated alkyl group and o depicts the number of carbon atoms, o is an integer from 1 to 12, and wherein m+o is an integer from 2 to 12; comprising reacting a fluorinated compound of formula (II) F(CF.sub.2).sub.n(CH.sub.2).sub.mX (II), wherein X is Cl, Br, I, MgCl, MgBr, or MgI, and n and m have the same meaning as in formula (I), with a non-fluorinated compound of formula (III) R.sub.oY (III), wherein Y is Cl, Br, I, MgCl, MgBr, or MgI, with the proviso that when X is Cl, Br or I, Y is MgCl, MgBr or MgI, and when X is MgCl, MgBr or MgI, Y is Cl, Br or I, and R.sub.o has the same meaning as in formula (I).

A process to prepare (9E,11Z)-9,11-hexadecadienyl acetate with a good yield and high purity of the general formula (1): CH.sub.3(CH.sub.2).sub.3CHCHCHCH(CH.sub.2).sub.aX.=The process includes a step of conducting a Wittig reaction between a haloalkenal of the general formula (2): OHCCHCH(CH.sub.2).sub.aX, and a triarylphosphonium pentylide of the general formula (3): CH.sub.3(CH.sub.2).sub.3CH.sup.P.sup.+Ar.sub.3, 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.

A process to prepare (9E,11Z)-9,11-hexadecadienyl acetate with a good yield and high purity of the general formula (1): CH.sub.3(CH.sub.2).sub.3CHCHCHCH(CH.sub.2).sub.aX.=The process includes a step of conducting a Wittig reaction between a haloalkenal of the general formula (2): OHCCHCH(CH.sub.2).sub.aX, and a triarylphosphonium pentylide of the general formula (3): CH.sub.3(CH.sub.2).sub.3CH.sup.P.sup.+Ar.sub.3, 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.

Methods selectively and efficiently produce 3,7-dimethyl-7-octenol and a carboxylic acid ester thereof. More specifically, a method produces 3,7-dimethyl-7-octenol, including steps of: subjecting a 3-methyl-3-butenyl nucleophilic reagent (2) and a 1,3-dihalo-2-methylpropane compound (3) to a coupling reaction to obtain a 2,6-dimethyl-6-heptenyl halide compound (4); converting the compound (4) into a 2,6-dimethyl-6-heptenyl nucleophilic reagent (5); and subjecting the nucleophilic reagent (5) to an addition reaction with at least one electrophilic reagent selected from the group made of formaldehyde, paraformaldehyde and 1,3,5-trioxane, followed by a hydrolysis reaction to obtain 3,7-dimethyl-7-octenol (6); and the other method. ##STR00001##

Methods selectively and efficiently produce 3,7-dimethyl-7-octenol and a carboxylic acid ester thereof. More specifically, a method produces 3,7-dimethyl-7-octenol, including steps of: subjecting a 3-methyl-3-butenyl nucleophilic reagent (2) and a 1,3-dihalo-2-methylpropane compound (3) to a coupling reaction to obtain a 2,6-dimethyl-6-heptenyl halide compound (4); converting the compound (4) into a 2,6-dimethyl-6-heptenyl nucleophilic reagent (5); and subjecting the nucleophilic reagent (5) to an addition reaction with at least one electrophilic reagent selected from the group made of formaldehyde, paraformaldehyde and 1,3,5-trioxane, followed by a hydrolysis reaction to obtain 3,7-dimethyl-7-octenol (6); and the other method. ##STR00001##