Synthetic Route of C9H9NO. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 3-Hydroxy-3-phenylpropanenitrile, is researched, Molecular C9H9NO, CAS is 17190-29-3, about Sulfonylisoxazolines: reliable intermediates for the preparation of β-hydroxy nitriles. Author is Wade, Peter A.; Bereznak, James F..
A series of six sulfonylisoxazolines, which were readily prepared via cycloaddition of PhSO2CNO to alkenes, were cleaved in 86-94% yield to β-hydroxy nitriles by the action of excess 2% Na-Hg. The stereochem. present at the isoxazoline C-4 and C-5 positions was retained during cleavage; since nitrile oxide cycloaddition to alkenes is a stereospecific process, the overall sequence permitted high diastereoselection. Under standard conditions, I gave a mixture of benzyl alc. and phenylacetonitrile rather than β-hydroxy nitriles; when the reactions were buffered, however, the β-hydroxy nitriles could be obtained in 88-91% yield. The β-hydroxy nitriles obtained from I rapidly underwent a retro-aldol reaction in the presence of aqueous base at room temperature The β-hydroxy nitrile obtained from 1-methylcyclopentene was epimerized by base and, at or above 80°, was cleaved to 6-oxoheptanenitrile.
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Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics