Nitric Acid → HCID 86720742, Verbindung
Reaktionsgleichung
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH2:9][C:10]#[N:11].[N+:12]([O-])([OH:14])=[O:13]>O>[CH3:1][C:2]1[CH:7]=[C:6]([N+:12]([O-:14])=[O:13])[C:5]([CH3:8])=[CH:4][C:3]=1[CH2:9][C:10]#[N:11]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To (2,5-dimethylphenyl)acetonitrile (30 g), under ice cooling, fuming nitric acid (103 mL) was added dropwise, and the resultant was stirred for 30 minutes under ice cooling. Water was added thereto, followed by extraction with ethyl acetate. The organic layer was dried over magnesium sulfate, and the desiccant was filtered off. Then, the solvent was distilled off under reduced pressure. A saturated aqueous solution of sodium bicarbonate was added to the obtained residue, followed by extraction with ethyl acetate. The organic layer was dried over magnesium sulfate, and the desiccant was filtered off. Then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH-type silica gel; chloroform/ethyl acetate-gradient elution=100/0→90/10) and then further purified twice by silica gel column chromatography (OH-type silica gel; hexane/ethyl acetate-gradient elution=90/10→60/40) to obtain the title compound (12 g) as a pale yellow solid.