Described herein is a process for the preparation of a mixture of compounds of formula ##STR00001##
having a weight ratio of the cis-diastereomers to trans-diastereoisomers higher than 1:1, where R.sub.1 represents a C.sub.1-8 alkyl group, a C.sub.2-8 alkenyl group or a C.sub.2-8 alkynyl group, each optionally substituted with one or two of a C.sub.1-4 alkyl alkoxy ether group and/or a C.sub.1-4 alkyl carboxylester group and R.sub.2 represents a C.sub.1-6 alkyl, a C.sub.2-6 alkenyl or a C.sub.2-6 alkynyl group, each optionally substituted with a C.sub.1-4 alkyl alkoxy ether group, a carboxylic acid group or a C.sub.1-4 alkyl carboxylester group and compounds suitable in the process.

Described herein is a process for the preparation of a mixture of compounds of formula ##STR00001##
having a weight ratio of the cis-diastereomers to trans-diastereoisomers higher than 1:1, where R.sub.1 represents a C.sub.1-8 alkyl group, a C.sub.2-8 alkenyl group or a C.sub.2-8 alkynyl group, each optionally substituted with one or two of a C.sub.1-4 alkyl alkoxy ether group and/or a C.sub.1-4 alkyl carboxylester group and R.sub.2 represents a C.sub.1-6 alkyl, a C.sub.2-6 alkenyl or a C.sub.2-6 alkynyl group, each optionally substituted with a C.sub.1-4 alkyl alkoxy ether group, a carboxylic acid group or a C.sub.1-4 alkyl carboxylester group and compounds suitable in the process.

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 provides a method for producing a bifunctional compound having a norbornane skeleton, the method comprising a step of hydroformylating a compound having an olefin with carbon monoxide and hydrogen, wherein the molar ratio of the carbon monoxide to the hydrogen during the reaction is 55/45 or more and 95/5 or less in the hydroformylating step.

The present invention provides a method for producing a bifunctional compound having a norbornane skeleton, the method comprising a step of hydroformylating a compound having an olefin with carbon monoxide and hydrogen, wherein the molar ratio of the carbon monoxide to the hydrogen during the reaction is 55/45 or more and 95/5 or less in the hydroformylating step.

The invention provides methods of preparing 8-hydroxy-2,2,14,14-tetramethylpentadecanedioic acid and methods of making a pharmaceutical material comprising a purified amount of 8-hydroxy-2,2,14,14-tetramethylpentadecanedioic acid. Also provided are compositions and pharmaceutical materials including a purified amount of 8-hydroxy-2,2,14,14-tetramethylpentadecanedioic acid as well as methods of treating various diseases and conditions using the compositions and pharmaceutical materials.

The invention provides methods of preparing 8-hydroxy-2,2,14,14-tetramethylpentadecanedioic acid and methods of making a pharmaceutical material comprising a purified amount of 8-hydroxy-2,2,14,14-tetramethylpentadecanedioic acid. Also provided are compositions and pharmaceutical materials including a purified amount of 8-hydroxy-2,2,14,14-tetramethylpentadecanedioic acid as well as methods of treating various diseases and conditions using the compositions and pharmaceutical materials.

The present invention discloses a method for preparing aldehydes or ketones via aerobic oxidation of alcohols with the copper salts and nitroxide radicals as catalysts. Both oxygen and air could be used as oxidants, after 4 to 48 hours of reaction in an organic solvent at room temperature, the alcohols are efficiently oxidized to the corresponding aldehydes or ketones. The present invention has the following advantages: easy to operate, refraining from using chlorides which are corrosive to equipment, readily available raw materials and reagents, mils reaction conditions, the broad substrate scope, good functional group tolerance, convenient purification, environmentally friendly and no pollution. Thus, the method is suitable for industrial production.

The present invention discloses a method for preparing aldehydes or ketones via aerobic oxidation of alcohols with the copper salts and nitroxide radicals as catalysts. Both oxygen and air could be used as oxidants, after 4 to 48 hours of reaction in an organic solvent at room temperature, the alcohols are efficiently oxidized to the corresponding aldehydes or ketones. The present invention has the following advantages: easy to operate, refraining from using chlorides which are corrosive to equipment, readily available raw materials and reagents, mils reaction conditions, the broad substrate scope, good functional group tolerance, convenient purification, environmentally friendly and no pollution. Thus, the method is suitable for industrial production.