Process for the alkoxycarbonylation of trivinylcyclohexane.

Disclosed are a compound represented by formula (I), a resin including a structural unit derived from the compound, and a resist composition: ##STR00001## wherein R.sup.1 represents an alkyl group which may have a halogen atom, a hydrogen atom or a halogen atom; A.sup.1 represents a single bond or *-A.sup.2-CO—O—; A.sup.2 and A.sup.3 represent an alkanediyl group; W represents a divalent monocyclic saturated alicyclic hydrocarbon group; R.sup.2 and R.sup.3 each represent a hydrogen atom or a hydrocarbon group which may have a fluorine atom, etc., R.sup.4 represents a hydrogen atom, —CH.sub.2— in the group may be replaced by —O—, —S—, etc., R.sup.2 and R.sup.3, or R.sup.2, R.sup.3 and R.sup.4 may be bonded each other to form a ring which may have a fluorine atom or an alkyl group.

Disclosed are a compound represented by formula (I), a resin including a structural unit derived from the compound, and a resist composition: ##STR00001## wherein R.sup.1 represents an alkyl group which may have a halogen atom, a hydrogen atom or a halogen atom; A.sup.1 represents a single bond or *-A.sup.2-CO—O—; A.sup.2 and A.sup.3 represent an alkanediyl group; W represents a divalent monocyclic saturated alicyclic hydrocarbon group; R.sup.2 and R.sup.3 each represent a hydrogen atom or a hydrocarbon group which may have a fluorine atom, etc., R.sup.4 represents a hydrogen atom, —CH.sub.2— in the group may be replaced by —O—, —S—, etc., R.sup.2 and R.sup.3, or R.sup.2, R.sup.3 and R.sup.4 may be bonded each other to form a ring which may have a fluorine atom or an alkyl group.

The present invention provides a process for preparing 2-(1,5,5-trimethyl-2-cyclopentenyl)ethyl acetate of the following formula (3), wherein Ac represents an acetyl group, the process comprising: subjecting a haloacetaldehyde alkyl 3,4,4-trimethyl-2-cyclopentenyl acetal compound of the following general formula (1), wherein R represents a linear or branched alkyl group having 1 to 4 carbon atoms, and Y represents a halogen atom, to a dehydrohalogenation reaction in the presence of a base, followed by a rearrangement reaction to obtain a (1,5,5-trimethyl-2-cyclopentenyl)acetate compound of the following general formula (2), wherein R is as defined above, and subjecting the alkoxycarbonylmethyl group (i.e., —CH.sub.2C(═O)OR) of the (1,5,5-trimethyl-2-cyclopentenyl)acetate compound (2) to a multi-step conversion to be converted into a 2-acetoxyethyl group (i.e., —CH.sub.2CH.sub.2OAc) to obtain 2-(1,5,5-trimethyl-2-cyclopentenyl)ethyl acetate (3).

##STR00001##

The present invention provides a process for preparing 2-(1,5,5-trimethyl-2-cyclopentenyl)ethyl acetate of the following formula (3), wherein Ac represents an acetyl group, the process comprising: subjecting a haloacetaldehyde alkyl 3,4,4-trimethyl-2-cyclopentenyl acetal compound of the following general formula (1), wherein R represents a linear or branched alkyl group having 1 to 4 carbon atoms, and Y represents a halogen atom, to a dehydrohalogenation reaction in the presence of a base, followed by a rearrangement reaction to obtain a (1,5,5-trimethyl-2-cyclopentenyl)acetate compound of the following general formula (2), wherein R is as defined above, and subjecting the alkoxycarbonylmethyl group (i.e., —CH.sub.2C(═O)OR) of the (1,5,5-trimethyl-2-cyclopentenyl)acetate compound (2) to a multi-step conversion to be converted into a 2-acetoxyethyl group (i.e., —CH.sub.2CH.sub.2OAc) to obtain 2-(1,5,5-trimethyl-2-cyclopentenyl)ethyl acetate (3).

##STR00001##

The present invention provides a process for preparing a (1,2-dimethyl-3-methylenecyclopentyl)acetate compound of the following general formula (3), wherein R represents a linear or branched alkyl group having 1 to 4 carbon atoms, the process comprising subjecting a haloacetaldehyde alkyl 2,3-dimethyl-2-cyclopentenyl acetal compound of the following general formula (1), wherein R is as defined above, and Y represents a halogen atom, to a dehydrohalogenation reaction in the presence of a base, followed by a rearrangement reaction to obtain a (1,2-dimethyl-2-cyclopentenyl)acetate compound of the following general formula (2), wherein R is as defined above, and subjecting the (1,2-dimethyl-2-cyclopentenyl)acetate compound (2) to an epoxidation reaction, followed by an isomerization reaction and then a methylenation reaction to obtain the (1,2-dimethyl-3-methylenecyclopentyl)acetate compound of the following general formula (3). The present invention also provides a process for preparing (1,2-dimethyl-3-methylenecyclopentyl)acetaldehyde of the following formula (4), the process comprising the aforesaid process for preparing the (1,2-dimethyl-3-methylenecyclopentyl)acetate compound (3), and converting an alkoxycarbonylmethyl group (i.e., —CH.sub.2C(═O)OR) of the (1,2-dimethyl-3-methylenecyclopentyl)acetate compound (3) to a formylmethyl group (i.e., —CH.sub.2CHO) to obtain (1,2-dimethyl-3-methylenecyclopentyl)acetaldehyde (4).

##STR00001##

The present invention provides a process for preparing a (1,2-dimethyl-3-methylenecyclopentyl)acetate compound of the following general formula (3), wherein R represents a linear or branched alkyl group having 1 to 4 carbon atoms, the process comprising subjecting a haloacetaldehyde alkyl 2,3-dimethyl-2-cyclopentenyl acetal compound of the following general formula (1), wherein R is as defined above, and Y represents a halogen atom, to a dehydrohalogenation reaction in the presence of a base, followed by a rearrangement reaction to obtain a (1,2-dimethyl-2-cyclopentenyl)acetate compound of the following general formula (2), wherein R is as defined above, and subjecting the (1,2-dimethyl-2-cyclopentenyl)acetate compound (2) to an epoxidation reaction, followed by an isomerization reaction and then a methylenation reaction to obtain the (1,2-dimethyl-3-methylenecyclopentyl)acetate compound of the following general formula (3). The present invention also provides a process for preparing (1,2-dimethyl-3-methylenecyclopentyl)acetaldehyde of the following formula (4), the process comprising the aforesaid process for preparing the (1,2-dimethyl-3-methylenecyclopentyl)acetate compound (3), and converting an alkoxycarbonylmethyl group (i.e., —CH.sub.2C(═O)OR) of the (1,2-dimethyl-3-methylenecyclopentyl)acetate compound (3) to a formylmethyl group (i.e., —CH.sub.2CHO) to obtain (1,2-dimethyl-3-methylenecyclopentyl)acetaldehyde (4).

##STR00001##

The present invention relates to a process for preparing a process for preparing a (2-cyclopentenyl)acetate ester compound of the following general formula (2): wherein R represents a linear or branched alkyl group having 1 to 4 carbon atoms, Y represents a halogen atom, and X.sub.1 to X.sub.7 represent, independently of each other, a hydrogen atom or a methyl group, with the proviso that one to three among X.sub.1 to X.sub.7 represent a methyl group and the remaining represent a hydrogen atom, the process comprising: subjecting a haloacetaldehyde alkyl 2-cyclopentenyl acetal compound of the following general formula (1): wherein R is as defined above, X.sub.1 to X.sub.7 are as selected in the general formula (2), respectively, and Y represents a halogen atom, to a dehydrohalogenation reaction in the presence of a base, followed by a rearrangement reaction to form the (2-cyclopentenyl)acetate ester compound (2) and a process for preparing a (2-cyclopentenyl)acetic acid compound of the following general formula (3): wherein X.sub.1 to X.sub.7 are as selected in the general formula (1), respectively, the process comprising hydrolyzing the (2-cyclopentenyl)acetate ester compound (2) to form the (2-cyclopentenyl)acetic acid compound (3). The present invention relates also to the novel compound, haloacetaldehyde alkyl 2-cyclopentenyl acetal compound (1).

##STR00001##

The present invention relates to a process for preparing a process for preparing a (2-cyclopentenyl)acetate ester compound of the following general formula (2): wherein R represents a linear or branched alkyl group having 1 to 4 carbon atoms, Y represents a halogen atom, and X.sub.1 to X.sub.7 represent, independently of each other, a hydrogen atom or a methyl group, with the proviso that one to three among X.sub.1 to X.sub.7 represent a methyl group and the remaining represent a hydrogen atom, the process comprising: subjecting a haloacetaldehyde alkyl 2-cyclopentenyl acetal compound of the following general formula (1): wherein R is as defined above, X.sub.1 to X.sub.7 are as selected in the general formula (2), respectively, and Y represents a halogen atom, to a dehydrohalogenation reaction in the presence of a base, followed by a rearrangement reaction to form the (2-cyclopentenyl)acetate ester compound (2) and a process for preparing a (2-cyclopentenyl)acetic acid compound of the following general formula (3): wherein X.sub.1 to X.sub.7 are as selected in the general formula (1), respectively, the process comprising hydrolyzing the (2-cyclopentenyl)acetate ester compound (2) to form the (2-cyclopentenyl)acetic acid compound (3). The present invention relates also to the novel compound, haloacetaldehyde alkyl 2-cyclopentenyl acetal compound (1).

##STR00001##

Provided herein are methods for the production of glycopyrronium tosylate and glycopyrronium tosylate compositions. Also provided herein are compositions useful in the production of glycopyrronium tosylate. Additionally provided herein are glycopyrronium tosylate compositions. Glycopyrronium tosylate is useful for the treatment of, among other conditions, hyperhidrosis.