Optically active 2,2′-biphenol derivative and production method of same
AssigneeNippon Soda Co., Ltd.
InventorsYoshikazu Ito, Yasushi Kubota, Tsutomu Inoue
Life of this patent
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Abstract
Disclosed herein are optically active biphenol derivatives represented by the following formulas (1) and (2), a method for optically resolving a biphenol derivative represented by formula (2′), a production method of an optically active biphenol derivative (1) comprising a step for reacting a Brønsted acid with a biphenol derivative (2), and a production method of an optically active biphenol derivative (3) comprising a step for reacting a Lewis acid with an optically active biphenol derivative (1) or an optically active biphenol derivative (2).
Claims12
A method for producing a 6,6′-disubstituted-2,2′-biphenol derivative represented by the following formula (3):
- wherein, R1 represents an optionally substituted primary or secondary alkyl group having 1 to 10 carbon atoms or an optionally substituted cycloalkyl group having 3 to 10 carbon atoms, and * represents an axially asymmetric center, comprising:
- allowing an optically active diamine to act on a 6,6′-disubstituted-5,5′-dihalogeno-3,3′-disubstituted-2,2′-biphenol derivative represented by the following formula (2′):
- wherein, R1 is the same as previously defined, R2 represents a tertiary alkyl group having 4 to 6 carbon atoms, and X represents a halogen atom, separating the resulting salt, and then neutralizing the salt to obtain an optically active 6,6′-disubstituted-5,5′-dihalogeno-3,3′-disubstituted-2,2′-biphenol derivative represented by the following formula (2):
- wherein, R1, R2, X and * are the same as previously defined, followed by further allowing a Lewis acid to act on the compound represented by formula (2).
A method for producing a 6,6′-disubstituted-2,2′-biphenol derivative represented by the following formula (3):
- wherein, R1 represents an optionally substituted primary or secondary alkyl group having 1 to 10 carbon atoms or an optionally substituted cycloalkyl group having 3 to 10 carbon atoms, and * represents an axially asymmetric center, comprising:
- allowing an optically active diamine to act on a 6,6′-disubstituted-5,5′-dihalogeno-3,3′-disubstituted-2,2′-biphenol derivative represented by the following formula (2′):
- wherein, R1 is the same as previously defined, R2 represents a tertiary alkyl group having 4 to 6 carbon atoms, and X represents a halogen atom, separating the resulting salt, and then neutralizing the salt to obtain an optically active 6,6′-disubstituted-5,5′-dihalogeno-3,3′-disubstituted-2,2′-biphenol derivative represented by the following formula (2):
- wherein, R1, R2, X and * are the same as previously defined, followed by allowing a Brønsted acid to act on the compound represented by formula (2) to obtain an optically active 6,6′-disubstituted-5,5′-dihalogeno-2,2′-biphenol derivative represented by the following formula (1):
- wherein, R1, X and * are the same as previously defined, and allowing a Lewis acid to act on the compound represented by formula (1).
A method for producing an optically active 6,6′-disubstituted-5,5′-dihalogeno-3,3′-disubstituted-2,2′-biphenol derivative represented by the following formula (2):
- wherein, R1 represents an optionally substituted primary or secondary alkyl group having 1 to 10 carbon atoms or an optionally substituted cycloalkyl group having 3 to 10 carbon atoms, R2 represents a tertiary alkyl group having 4 to 6 carbon atoms, X represents a halogen atom, and * represents an axially asymmetric center, comprising:
- allowing an optically active diamine compound to act on an a 6,6′-disubstituted-5,5′-dihalogeno-3,3′-disubstituted-2,2′-biphenol derivative represented by the following formula (2′):
- wherein, R1, R2 and X are the same as previously defined, separating the resulting salt, and then neutralizing the salt.
An optically active 2,2′-biphenol derivative represented by the following formula (1):
- wherein, R1 represents an optionally substituted primary or secondary alkyl group having 1 to 10 carbon atoms or an optionally substituted cycloalkyl group having 3 to 10 carbon atoms, X represents a halogen atom, and * represents an axially asymmetric center.
An optically active 2,2′-biphenol derivative represented by the following formula (2):
- wherein, R1 represents an optionally substituted primary or secondary alkyl group having 1 to 10 carbon atoms or an optionally substituted cycloalkyl group having 3 to 10 carbon atoms, R2 represents a tertiary alkyl group having 4 to 6 carbon atoms, X represents a halogen atom, and * represents an axially asymmetric center.
A 2,2′-biphenol derivative represented by the following formula (2′):
- wherein, R1 represents an optionally substituted primary or secondary alkyl group having 1 to 10 carbon atoms or an optionally substituted cycloalkyl group having 3 to 10 carbon atoms, R2 represents a tertiary alkyl group having 4 to 6 carbon atoms, and X represents a halogen atom.
A method for producing a 6,6′-disubstituted-5,5′-dihalogeno-2,2′-biphenol derivative represented by following formula (2′):
- wherein, R1 represents an optionally substituted primary or secondary alkyl group having 1 to 10 carbon atoms or an optionally substituted cycloalkyl group having 3 to 10 carbon atoms, R2 represents a tertiary alkyl group having 4 to 6 carbon atoms, and X represents a halogen atom, comprising:
- allowing a copper salt and an organic base or cupric oxyhalide organic base complex to act on a 5-substituted-4-halogeno-2-substituted-phenol derivative represented by the following formula (4):
- wherein, R1, R2 and X are the same as previously defined.
A method for producing an optically active 6,6′-disubstituted-5,5′-dihalogeno-2,2′-biphenol derivative represented by the following formula (1):
- wherein, R1 represents an optionally substituted primary or secondary alkyl group having 1 to 10 carbon atoms or an optionally substituted cycloalkyl group having 3 to 10 carbon atoms, X represents a halogen atom, and * represents an axially asymmetric center, comprising:
- allowing a Brønsted acid to act on an optically active 6,6′-disubstituted-5,5′-dihalogeno-3,3′-disubstituted-2,2′-biphenol derivative represented by the following formula (2):
- wherein, R1, X and * are the same as previously defined, and R2 represents a tertiary alkyl group having 4 to 6 carbon atoms.
A method for producing an optically active 6,6′-disubstituted-2,2′-biphenol derivative represented by the following formula (3):
- wherein, R1 represents an optionally substituted primary or secondary alkyl group having 1 to 10 carbon atoms or an optionally substituted cycloalkyl group having 3 to 10 carbon atoms, and * represents an axially asymmetric center, comprising:
- allowing a Lewis acid to act on an optically active 6,6′-disubstituted-5,5′-dihalogeno-2,2′-biphenol derivative represented by the following formula (1):
- wherein, R1 and * are the same as previously defined, and X represents a halogen atom.
Dependencies are inferred from the claim text.