Process for producing vitamin A aldehyde and intermediate for producing the same
AssigneeSumitomo Chemical Company, Limited
InventorsShinzo Seko, Naoto Konya, Toshiya Takahashi
Life of this patent
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Abstract
There are disclosed an alcohol derivative of formula (1): wherein Ar is an optionally substituted aryl group and R is a straight or branched C1-C3 lower alkyl group, and the wavy line depicted by indicates a single bond and stereochemistry relating to a double bond bound therewith is E or Z or a mixture thereof, and a process for producing the same and a process for producing Vitamin A aldehyde using the same.
Claims9
A method for producing an alcohol derivative of formula (1):
- wherein
- Ar is an aryl group, which may be substituted with a substituent group selected from
- a C1-C5 alkyl group, a C1-C5 alkoxy group, a halogen atom and a nitro group,
- R is a straight or branched C1-C3 lower alkyl group, and the wavy line depicted by
- indicates a single bond and stereochemistry relating to a double bond bound therewith is E or Z or a mixture thereof,
- which comprises reacting a diol derivative of formula (2):
- wherein Ar and the wavy line represent the same as defined above, with a lower alcohol of formula:
- ROH (3)
- wherein R is a straight or branched C1-C3 lower alkyl group, in the presence of an acid catalyst.
A method for producing an aldehyde derivative of formula (4):
- wherein
- Ar is an aryl group, which may be substituted with a substituent group selected from
- a C1-C5 alkyl group, a C1-C5 alkoxy group, a halogen atom and a nitro group,
- R is a straight or branched C114 C3 lower alkyl group, and the wavy line depicted by
- indicates a single bond and stereochemistry relating to a double bond bound therewith is E or Z or a mixture thereof,
- which comprises reacting an alcohol derivative of formula (1):
- wherein Ar, R and the wavy line represent the same as defined above, with an oxidizing agent optionally in the presence of a catalyst.
A method for producing Vitamin A aldehyde of formula (5):
- wherein the wavy line depicted by
- indicates a single bond and stereochemistry relating to a double bond bound therewith is E or Z or a mixture thereof, which comprises the steps of:
- reacting a diol derivative of formula (2):
- wherein
- Ar is an aryl group, which may be substituted with a substituent group selected from
- a C1-C5 alkyl group, a C1-C5 alkoxy group, a halogen atom and a nitro group, and the wavy line represents the same as defined above, with a lower alcohol of formula:
- ROH (3)
- wherein R is a straight or branched C1-C3 lower alkyl group, in the presence of an acid catalyst, to produce an alcohol derivative of formula (1):
- wherein Ar, R and the wavy line represent the same as defined above,
- reacting the alcohol derivative of formula (1) with an oxidizing agent optionally in the presence of a catalyst to produce an aldehyde derivative of formula (4):
- wherein Ar, R and the wavy line represent the same as defined above, and reacting the aldehyde derivative of formula (4) with a base.
Dependencies are inferred from the claim text.