Propanal → Benzenepentanal, .alpha.-methyl-
Reaction equation
[C:1]1([CH2:7][CH2:8][CH:9]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:11](=[O:14])[CH2:12][CH3:13]>>[CH3:13][CH:12]([CH2:9][CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH:11]=[O:14]Participants
Procedure
The 2-methyl-5-phenyl aldehyde derivatives are conveniently prepared by a number of methods known in the art. For example, by an Aldol condensation between 3-phenylpropanal and proprionaldehyde, followed by hydrogenation of the resulting α,β-unsaturated aldehyde to form the saturated aldehyde, 2-methyl-5-phenylpentanal. This aldehyde is the direct precursor for the alcohol, 2-methyl-5-phenylpentan-1-ol via reduction with, e.g. sodium borohydride, as well as the nitrile, 2,4-dimethyl-5-phenyl-pentanitrile via oxidation dehydration chemistry by reaction of hydroxylamine/formic acid as described above. Alternatively, aldehyde derivatives may be prepared by oxidation of the corresponding primary alcohol, i.e. 2-methyl-5-phenylpentan-1-ol, a known compound. The corresponding nitrile, 2-methyl-5-phenylpentanenitrile, is prepared by converting the aldehyde via reaction with hydroxylamine to form the aldoxime intermediate and subsequent formic acid catalyzed dehydration. The primary alcohol may also be converted to the corresponding acid as described above.
Sources & evidence
- ORD record
- ord-d70a4e15242e49e7a33698067f7cb823
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06310033B1
Reaction notes
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