Shin-etsu Chemical Co., Ltd.

Other

Yusuke Nagae

Takeshi Kinsho

Yuki Miyake

Naoki Ishibashi

Akihiro Baba

Tomohiro Watanabe

Takeru Watanabe

Miyoshi Yamashita

Tatsuya Hojo

Shogo Tsukaguchi

Yasuhiko Kutsuwada

The present invention relates to a process for preparing a (4Z)-11,11-dialkoxy-4-undecenyltriarylphosphonium halide compound of the following general formula (3-Z): wherein Y represents a halogen atom, Ar represents, independently of each other, an aryl group, and Rand Rrepresent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, or Rand Rmay form together a divalent hydrocarbon group, R-R, having 2 to 10 carbon atoms, the process comprising: subjecting a (7Z)-11-halo-1,1-dialkoxy-7-undecene compound of the following general formula (1-Z): wherein Xrepresents a halogen atom, and Rand Rare as defined above to a phosphonium salt formation reaction with a phosphine compound of the following general formula (2): wherein Ar is as defined above to form the (4Z)-11,11-dialkoxy-4-undecenyltriarylphosphonium halide compound (3-Z).

11-halo-1,1-dialkoxy-7-undecene compound and processes for preparing a 11,11-dialkoxy-4-undecenyltriarylphosphonium halide compound, a trienal compound, and a dienal compound

Provided is a 3-acyloxymethyl-3-butenal acetal compound of General Formula (10): wherein Rand R, 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 Xis an acyloxy group having 1 to 6 carbon atoms.

3-acyloxymethyl-3-butenal acetal compounds

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): wherein Rand R, 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).

Methods of producing 7-methyl-3-methylene-7-octenal acetal compounds

The present invention provides a process for preparing a diester compound of the following general formula (1), having a dimethylcyclobutane ring, wherein Rand Rrepresent, 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 Ris as defined above, with a phosphonic ester compound of the following general formula (3), wherein Rand Rrepresent, independently of each other, a monovalent hydrocarbon group having 1 to 10 carbon atoms, to produce the diester compound (1), having a dimethylcyclobutane ring.

Diester compound having a dimethylcyclobutane ring, a process for preparing the same, and a process for preparing dimethylcyclobutane compound derived from the diester compound

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).

Dimethylcyclobutanone compounds, dimethylcyclobutane compounds, and processes for preparing the same

The present invention relates to a 6-hydroxy-3-hexenyl alkoxymethyl ether compound of the following general formula (1): HOCHCHCH=CHCHCHOCHOCHR(1), Rrepresenting 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): CH(CH)CH—CH(CH)CH═CHCHCHOH (6) from the 6-hydroxy-3-hexenyl alkoxymethyl ether compound (1).

6-hydroxy-3-hexenyl alkoxymethyl ether compound and a process for preparing a 3,13-octadecadien-1-ol compound from the same

The present invention provides a process for preparing 2-methyl-N-(2′-methylbutyl)butanamide of the following formula (1): the process comprising: subjecting an α-arylethyl-2-methylbutylamine compound of the following general formula (2): wherein Ar represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, to N-2-methylbutyrylation to form an N-α-arylethyl-2-methyl-N-(2′-methylbutyl)butanamide compound of the following general formula (3): wherein Ar is as defined above, and removing the α-arylethyl group of the resulting compound (3) to form 2-methyl-N-(2′-methylbutyl)butanamide (1).

Process for preparing 2-methyl-N-(2′-methylbutyl)butanamide

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 Mrepresents Li, MgZ, ZnZ, Cu, CuZ, or CuLiZ, wherein Zrepresents 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 Xrepresents 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).

Process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate and intermediates thereof

A method for producing a 7-methyl-3-methylene-7-octenyl carboxylate compound (1), the method including the step of coupling a nucleophilic reagent of General Formula (8): wherein M is a cationic moiety, with an acetal compound of General Formula (9): wherein Rand R, 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 is a leaving group, to obtain the 7-methyl-3-methylene-7-octenal acetal compound.

Method for producing 7-methyl-3-methylene-7-octenal acetal compound

The present invention relates to a process for preparing a 3-isopropenyl-6-heptenal compound of the following formula (2): wherein Rrepresents a hydrogen atom or a methyl group, the process comprising: subjecting a 3-isopropenyl-6-heptenoate ester compound of the following formula (1): wherein Ris as defined above, and Rrepresents 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).

Processes for preparing a 3-isopropenyl-6-heptenal compound and a 6- isopropenyl-3-methyl-3,9-decadienyl carboxylate compound, and an intermediate therefor

The present invention relates to a process for preparing a (1S,2R)-(2-hydroxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound of the following general formula (S,R)-(2), wherein Rrepresents a monovalent hydrocarbon group having 1 to 6 carbon atoms, and a bold wedged bond represents the absolute configuration, and a (1R,2S)-(2-acetoxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound of the following general formula (R,S)-(3), wherein Ris as defined above, a hashed wedged bond represents the absolute configuration, and Ac represents an acetyl group, the process comprising: subjecting a (1RS,2SR)-(2-hydroxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound of the following general formula (RS,SR)-(2), wherein Ris as defined above, and a hashed unwedged bond represents a relative configuration, to a kinetic resolution reaction with a lipase in the presence of vinyl acetate to obtain the (1S,2R)-(2-hydroxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound ((S,R)-(2)) and the (1R,2S)-(2-acetoxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound ((R,S)-(3)).

Kinetic resolution reaction of a (1RS,2SR)-(2-hydroxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound, a process for preparing optically active trans-&#x3b1;-necrodyl isobutyrate, and a process for preparing optically active &#x3b3;-necrodyl isobutyrate

The present invention relates to a 6-hydroxy-3-hexenyl alkoxymethyl ether compound of the following general formula (1): HOCHCHCH&#x2550;CHCHCHOCHOCHR' (1), Rrepresenting 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): CH(CH)CH&#x2550;CH(CH)CH&#x2550;CHCHCHOH (6) from the 6-hydroxy-3-hexenyl alkoxymethyl ether compound (1).

The present invention provides a process for preparing 2-methyl-N-(2'-methylbutyl) butanamide of the following formula (1):the process comprising: subjecting an &#x3b1;-arylethyl-2-methylbutylamine compound of the following general formula (2): wherein Ar represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, to N-2-methylbutyrylation to form an N-&#x3b1;-arylethyl-2-methyl-N-(2&#x2032;-methylbutyl)butanamide compound of the following general formula (3): wherein Ar is as defined above, and removing the &#x3b1;-arylethyl group of the resulting compound (3) to form 2-methyl-N-(2&#x2032; -methylbutyl)butanamide (1). 

Process for preparing 2-methyl-N-(2'-methylbutyl)butanamide

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 Mrepresents Li, MgZ, ZnZ, Cu, CuZ, or CuLiZ, wherein Zrepresents 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 Xrepresents 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). 

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). 

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Niigata, Japan

Yusuke Nagae