Process for producing .beta.-carotene, and intermediate compounds useful for the process
AssigneeKuraray Co., Ltd.
InventorsToshiki Mori, Hiroshi Fujii, Takashi Onishi, Kazuo Yamamoto
Life of this patent
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Abstract
Provided is a novel process for readily producing .beta.-carotene by reacting a sulfone compound represented by the general formula (1), (2) or (3) with an alkali, ##STR1## wherein R represents a phenyl group which may be substituted, R' a protecting group of acetal type and X a halogen atom.
Claims28
A process for producing .beta.-carotene, comprising oxidizing a sulfone alcohol selected from the group consisting of formula (IV), formula (V) and formula (VI):
- ##STR31## wherein R represents a phenyl group or a substituted phenyl group, R' represents an acetal protecting group, and X represents a halogen atom, with manganese dioxide at a temperature of from 10.degree. C. to 50.degree. C. for a length of time of from 30 minutes to 10 hours in a solvent selected from the group consisting of benzene, toluene, halohydrocarbons, ethers and esters to obtain a sulfone aldehyde,
- coupling said sulfone aldehyde selected from the group consisting of formula (VII), formula (VIII) and formula (IX) with a phosphonium salt of vitamin A:
- ##STR32## wherein R, R' and X are as defined above, to obtain a sulfone compound represented by the group consisting of formula (I), formula (II) and formula (III):
- ##STR33## wherein R, R' and X are as defined above, and reacting said sulfone compound with an alkali.
A process for producing .beta.-carotene, comprising oxidizing a sulfone alcohol selected from the group consisting of formula (IV), formula (V) and formula (VI):
- ##STR34## wherein R represents a phenyl group or a substituted phenyl group, R' represents an acetal protecting group, and X represents a halogen atom, with a mixture of aluminum catalyst and a tertiary aldehyde at a temperature of from 10.degree. C. to 60.degree. C. for a length of time of from 30 minutes to 6 hours to obtain a sulfone aldehyde,
- coupling said sulfone aldehyde selected from the group consisting of formula (VII), formula (VIII) and formula (IX) with a phosphonium salt of vitamin A:
- ##STR35## wherein R, R' and X are as defined above, to obtain a sulfone compound represented by the group consisting of formula (I), formula (II) and formula (III):
- ##STR36## wherein R, R' and X are as defined above, and reacting said sulfone compound with an alkali.
A process for producing a sulfone aldehyde of the formula (VII) ##STR37## wherein R represents a phenyl group or a substituted phenyl group and X represents a halogen atom, comprising oxidizing a sulfone alcohol of the formula (IV) ##STR38## wherein R and X are as defined above, with manganese dioxide at a temperature of from 10.degree. C. to 50.degree. C. for a length of time of from 30 minutes to 10 hours in a solvent selected from the group consisting of benzene, toluene, halohydrocarbons, ethers and esters.
A process for producing a sulfone aldehyde of the formula (VII) ##STR39## wherein R represents a phenyl group or a substituted phenyl group and X represents a halogen atom, comprising oxidizing a sulfone alcohol of the formula (IV) ##STR40## wherein R and X are as defined above, with a mixture of aluminum catalyst and a tertiary aldehyde at a temperature of from 10.degree. C. to 60.degree. C. for a length of time of from 30 minutes to 6 hours.
A process for producing a sulfone aldehyde of the formula (VIII) ##STR41## wherein R represents a phenyl group or a substituted phenyl group and X represents a halogen atom, comprising oxidizing a sulfone alcohol of the formula (V) ##STR42## wherein R and X are as defined above, with manganese dioxide at a temperature of from 10.degree. C. to 50.degree. C. for a length of time of from 30 minutes to 10 hours in a solvent selected from the group consisting of benzene, toluene, halohydrocarbons, ethers and esters.
A process for producing a sulfone aldehyde of the formula (VIII) ##STR43## wherein R represents a phenyl group or a substituted phenyl group and X represents a halogen atom, comprising oxidizing a sulfone alcohol of the formula (V) ##STR44## wherein R and X are as defined above, with a mixture of aluminum catalyst and a tertiary aldehyde at a temperature of from 10.degree. C. to 60.degree. C. for a length of time of from 30 minutes to 6 hours.
A process for producing a sulfone aldehyde of the formula (IX) ##STR45## wherein R represents a phenyl group or a substituted phenyl group and X represents a halogen atom, comprising oxidizing a sulfone alcohol of the formula (VI) ##STR46## wherein R and X are as defined above, with manganese dioxide at a temperature of from 10.degree. C. to 50.degree. C. for a length of time of from 30 minutes to 10 hours in a solvent selected from the group consisting of benzene, toluene, halohydrocarbons, ethers and esters.
A process for producing a sulfone aldehyde of the formula (IX) ##STR47## wherein R represents a phenyl group or a substituted phenyl group and X represents a halogen atom, comprising oxidizing a sulfone alcohol of the formula (VI) ##STR48## wherein R and X are as defined above, with a mixture of aluminum catalyst and a tertiary aldehyde at a temperature of from 10.degree. C. to 60.degree. C. for a length of time of from 30 minutes to 6 hours.
A process for producing a sulfone of the formula (I) ##STR49## wherein R represents a phenyl group or a substituted phenyl group and X represents a halogen atom, comprising oxidizing a sulfone alcohol of the formula (IV) ##STR50## wherein R and X are as defined above, with manganese dioxide at a temperature of from 10.degree. C. to 50.degree. C. for a length of time of from 30 minutes to 10 hours in a solvent selected from the group consisting of benzene, toluene, halohydrocarbons, ethers and esters, to obtain a sulfone aldehyde of the formula (VII) ##STR51## and coupling said sulfone aldehyde of the formula (VII) with a phosphonium salt of vitamin A.
A process for producing a sulfone of the formula (I) ##STR52## wherein R represents a phenyl group or a substituted phenyl group and X represents a halogen atom, comprising oxidizing a sulfone alcohol of the formula (IV) ##STR53## wherein R and X are as defined above, with a mixture of aluminum catalyst and a tertiary aldehyde at a temperature of from 10.degree. C. to 60.degree. C. for a length of time of from 30 minutes to 6 hours to obtain a sulfone aldehyde of the formula (VII) ##STR54## and coupling said sulfone aldehyde of the formula (VII) with a phosphonium salt of vitamin A.
A process for producing a sulfone of the formula (II) ##STR55## wherein R represents a phenyl group or a substituted phenyl group and X represents a halogen atom, comprising oxidizing a sulfone alcohol of the formula (V) ##STR56## wherein R and X are as defined above, with manganese dioxide at a temperature of from 10.degree. C. to 50.degree. C. for a length of time of from 30 minutes to 10 hours in a solvent selected from the group consisting of benzene, toluene, halohydrocarbons, ethers and esters, to obtain a sulfone aldehyde of the formula (VIII) ##STR57## and coupling said sulfone aldehyde of the formula (VIII) with a phosphonium salt of vitamin A.
A process for producing a sulfone of the formula (II) ##STR58## wherein R represents a phenyl group or a substituted phenyl group and X represents a halogen atom, comprising oxidizing a sulfone alcohol of the formula (V) ##STR59## wherein R and X are as defined above, with a mixture of aluminum catalyst and a tertiary aldehyde at a temperature of from 10.degree. C. to 60.degree. C. for a length of time of from 30 minutes to 6 hours to obtain a sulfone aldehyde of the formula (VIII) ##STR60## and coupling said sulfone aldehyde of the formula (VIII) with a phosphonium salt of vitamin A.
A process for producing a sulfone of the formula (III) ##STR61## wherein R represents a phenyl group or a substituted phenyl group and X represents a halogen atom, comprising oxidizing a sulfone alcohol of the formula (VI) ##STR62## wherein R and X are as defined above, with manganese dioxide at a temperature of from 10.degree. C. to 50.degree. C. for a length of time of from 30 minutes to 10 hours in a solvent selected from the group consisting of benzene, toluene, halohydrocarbons, ethers and esters, to obtain a sulfone aldehyde of the formula (IX) ##STR63## and coupling said sulfone aldehyde of the formula (IX) with a phosphonium salt of vitamin A.
A process for producing a sulfone of the formula (III) ##STR64## wherein R represents a phenyl group or a substituted phenyl group and X represents a halogen atom, comprising oxidizing a sulfone alcohol of the formula (VI) ##STR65## wherein R and X are as defined above, with a mixture of aluminum catalyst and a tertiary aldehyde at a temperature of from 10.degree. C. to 60.degree. C. for a length of time of from 30 minutes to 6 hours to obtain a sulfone aldehyde of the formula (IX) ##STR66## and coupling said sulfone aldehyde of the formula (IX) with a phosphonium salt of vitamin A.
Dependencies are inferred from the claim text.