Nitric Acid → 3-Cyanomethyl-1-nitro-2,4,6-trimethylbenzene

Reaktionsgleichung

[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[CH2:10][C:11]#[N:12].[N+:13]([O-])([OH:15])=[O:14].OS(O)(=O)=O>C(O)(=O)C>[C:11]([CH2:10][C:3]1[C:4]([CH3:9])=[C:5]([N+:13]([O-:15])=[O:14])[C:6]([CH3:8])=[CH:7][C:2]=1[CH3:1])#[N:12]

Komponenten

Versuchsvorschrift

To a suspension of 2,4,6-trimethylphenylacetonitrile (4.5 g) in acetic acid (40 mL) at RT was added dropwise 70% HNO3 (20 mL) and conc. H2SO4 (5 mL). The brown reaction mixture was stirred for 1 h, poured into ice-water (500 mL). The product was extracted into ethyl acetate, the extract was washed with water, dried over MgSO4 and concentrated to give 3-cyanomethyl-1-nitro-2,4,6-trimethylbenzene as an oil (5.8 g, quantitative yield).