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##

Provided herein are formulations of plated powders of acetaldehyde precursors. Also provided herein are methods of making and using the powders.

Provided herein are formulations of plated powders of acetaldehyde precursors. Also provided herein are methods of making and using the powders.

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##

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##

A method for producing 7-methyl-3-methylene-7-octenal of Formula (2) is provided and includes a step of hydrolyzing a 7-methyl-3-methylene-7-octenal acetal compound of General Formula (1):

##STR00001##

wherein R.sup.1 and R.sup.2, which may be the same or different, are each analkyl group having 1 to 6 carbon atoms, or are bonded to each other to form a divalent alkylene group having 2 to 12 carbon atoms to obtain the 7-methyl-3-methylene-7-octenal (2).

A method for producing 7-methyl-3-methylene-7-octenal of Formula (2) is provided and includes a step of hydrolyzing a 7-methyl-3-methylene-7-octenal acetal compound of General Formula (1):

##STR00001##

wherein R.sup.1 and R.sup.2, which may be the same or different, are each analkyl group having 1 to 6 carbon atoms, or are bonded to each other to form a divalent alkylene group having 2 to 12 carbon atoms to obtain the 7-methyl-3-methylene-7-octenal (2).

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-CR.sup.1CR.sup.2(CH.sub.2).sub.2CCH (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-CR.sup.1CR.sup.2(CH.sub.2).sub.2-X.sup.1 (1) and (ii) an alkyne compound of the following formula (2): X.sup.2=CCSi(R.sup.3)(R.sup.4)(R.sup.5) (2) to a coupling reaction to form a silane compound of the following formula (3): Y-Z-CR.sup.1CR.sup.2(CH.sub.2).sub.2CCSi(R.sup.3)(R.sup.4)(R.sup.5) (3); and subjecting the silane compound (3) to a desilylation reaction to form the 5-alken-1-yne compound (4).

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-CR.sup.1CR.sup.2(CH.sub.2).sub.2CCH (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-CR.sup.1CR.sup.2(CH.sub.2).sub.2-X.sup.1 (1) and (ii) an alkyne compound of the following formula (2): X.sup.2=CCSi(R.sup.3)(R.sup.4)(R.sup.5) (2) to a coupling reaction to form a silane compound of the following formula (3): Y-Z-CR.sup.1CR.sup.2(CH.sub.2).sub.2CCSi(R.sup.3)(R.sup.4)(R.sup.5) (3); and subjecting the silane compound (3) to a desilylation reaction to form the 5-alken-1-yne compound (4).

Provided is a 3-acyloxymethyl-3-butenal acetal compound of General Formula (10):

##STR00001##

wherein R.sup.1 and R.sup.2, which may be the same or different, are each an alkyl group having 1 to 6 carbon atoms, or are bonded to each other to form a divalent alkylene group having 2 to 12 carbon atoms, and X.sup.1 is an acyloxy group having 1 to 6 carbon atoms.