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

HRID 987844Notes

Reaction equation

HRID 987844 reaction equation
[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]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 5206982,4,6-Trimethylphenylacetonitrile

Product 1

HCID 106796973-Cyanomethyl-1-nitro-2,4,6-trimethylbenzene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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 yleld).

Workup

  1. extractionThe product was extracted into ethyl acetate
  2. washthe extract was washed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-da8b7b5b99284defa9a54abbed672b4a
Source dataset
uspto-grants-2003_10
Patent number
US06632829B2

Reaction notes

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