Nitric Acid → 4-Methyl-3-nitrobenzonitrile
Reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]#[N:13])=[CH:8][CH:7]=1>S(=O)(=O)(O)O>[CH3:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]#[N:13])=[CH:8][C:7]=1[N+:1]([O-:4])=[O:2]Participants
4
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
In a 250 ml flask, 10 g of 4-methylbenzenecarbonitrile was dissolved in 30 ml of concentrated sulfuric acid and then cooled to 0° C. 7 ml of nitric acid mixed with 10 ml of concentrated sulfuric acid was slowly added thereto over one hour at −2° C. to 0° C. The reaction solution was poured into ice water and then stirred. The resulting precipitate was filtered, washed three times with water and then dried. The residue was purified with silica gel column chromatography [eluent: ethyl acetate/n-hexane(1:3)]. The fractions containing the desired product were combined and then evaporated to obtain 11.2 g of the title compound as a white solid.
Workup
- additionwas slowly added
- filtrationThe resulting precipitate was filtered
- washwashed three times with water
- customdried
- customThe residue was purified with silica gel column chromatography [eluent: ethyl acetate/n-hexane(1:3)]
- additionThe fractions containing the desired product
- customevaporated
Sources & evidence
- ORD record
- ord-a025954daf144724a5cadb0b05551001
- Source dataset
- uspto-grants-2001_03
- Patent number
- US06201006B1
Reaction notes
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