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AssigneeMitsubishi Gas Chemical Company, Inc.
InventorsMitsuharu Kitamura, Junya Nishiuchi, Norio Fushimi
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A process for effectively producing a 4-(4-alkylcyclohexyl)benzaldehyde, 4-(cyclohexyl)benzaldehyde, a 4-(trans-4-alkylcyclohexyl)benzaldehyde and a (trans-4-alkylcyclohexyl)benzene useful for electronic material applications such as liquid crystals and for pharmaceutical and agrochemical applications, etc., are disclosed. The present invention provides (1) a process for producing a 4-(4-alkylcyclohexyl)benzaldehyde or 4-(cyclohexyl)benzaldehyde by formylating a (4-alkylcyclohexyl)benzene or cyclohexylbenzene with carbon monoxide, (2) a process for producing a 4-(trans-4-alkylcyclohexyl)benzaldehyde by formylating a (4-alkylcyclohexyl)benzene having a cis/trans molar ratio of 0.3 or less with carbon monoxide, and (3) a process for producing a (trans-4-alkylcyclohexyl)benzene by isomerizing a mixture of the cis and trans isomers of a (4-alkylcyclohexyl)benzene, all of the processes being performed in the presence of HF and BF3.
A process for producing a 4-(4-alkylcyclohexyl)-benzaldehyde or 4-(cyclohexyl)benzaldehyde, comprising formylating a benzene derivative represented by the following formula (1a) with carbon monoxide in the presence of hydrogen fluoride and boron trifluoride to obtain a 4-(4-alkylcyclohexyl)benzaldehyde represented by the following formula (2) or 4-(cyclohexyl)benzaldehyde,
4-(4-n-Butylcyclohexyl)benzaldehyde represented by the following formula (3):
A process for producing a 4-(trans-4-alkylcyclohexyl)benzaldehyde, comprising formylating a (4-alkylcyclohexyl)benzene represented by the following formula (1b) and having a cis/trans molar ratio of 0.3 or less with carbon monoxide in the presence of hydrogen fluoride and boron trifluoride to obtain a 4-(trans-4-alkylcyclohexyl)benzaldehyde represented by the following formula (4),
A 4-(trans-4-alkylcyclohexyl)benzaldehyde having a 4-(4-alkylcyclohexyl)benzaldehyde purity of 98% or more and a trans isomer purity of 99% or more.
A process for producing a (trans-4-alkylcyclohexyl)benzene represented by the following formula (5),
A process for producing a 4-(trans-4-alkylcyclohexyl)benzaldehyde, comprising isomerizing a mixture of the cis and trans isomers of a (4-alkylcyclohexyl)benzene represented by the following formula (1b) in the presence of hydrogen fluoride and boron trifluoride to obtain a (trans-4-alkylcyclohexyl)benzene represented by the following formula (5), and then, continuedly, formylating the (trans-4-alkylcyclohexyl)benzene with carbon monoxide to obtain a 4-(trans-4-alkylcyclohexyl)benzaldehyde represented by the following formula (4),
Dependencies are inferred from the claim text.