Nitric Acid → 4-Methyl-3-nitrobenzonitrile

HRID 1584087Notes

Reaction equation

HRID 1584087 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[N+:10]([O-])([OH:12])=[O:11]>>[N+:10]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[CH3:1])[C:6]#[N:7])([O-:12])=[O:11]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 7724p-Tolunitrile

Product 1

HCID 5893334-Methyl-3-nitrobenzonitrile

Procedure

399 g (2.56 mol) of 4-methylbenzonitrile were added over the course of 90 min into 1 l of fuming nitric acid at -10° C. 1 h after the addition, the mixture was poured into 2.5 l of ice-water, whereupon a solid precipitated and was separated off on a suction filter funnel and washed to neutral pH with water. The yield was 363 g (88%). 1H-NMR (CDCl3 ; δ in ppm): 8.3 (d,1H); 7.8 (dd, 1H); 7.5 (dd, 1H); 2.7 (s, 3H)

Workup

  1. addition1 h after the addition
  2. customprecipitated
  3. customwas separated off on a suction
  4. filtrationfilter funnel
  5. washwashed to neutral pH with water

Sources & evidence

ORD record
ord-4212dfbb679245bca6f817ce33fbd9b0
Source dataset
uspto-grants-1999_08
Patent number
US05932567

Reaction notes

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