Nitric Acid → 4-Methyl-3-nitrobenzonitrile

HRID 1981111Notes

Reaction equation

HRID 1981111 reaction equation
S(=O)(=O)(O)O.[C:6]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)#[N:7].[N+:15]([O-])([OH:17])=[O:16]>>[CH3:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]#[N:7])=[CH:9][C:10]=1[N+:15]([O-:17])=[O:16]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 7724p-Tolunitrile

Product 1

HCID 5893334-Methyl-3-nitrobenzonitrile

Procedure

An amount of 240 parts by weight of concentrated sulfuric acid was cooled to -5° C. in a reaction vessel equipped with a drip funnel, agitator and thermometer. While stirring the mixture well, 40 parts by weight of 4-cyanotoluene were added portionwise and 25 volume parts of concentrated nitric acid were then added dropwise at a temperature between -5° C. and +5° C. To complete the nitration, the mixture was agitated at 0° C. for two hours and the reaction mixture was then poured onto 400 parts by weight of ice. The precipitate was recovered by filtration, thoroughly washed with water and dried in air. The result was 50.9 parts by weight of 1-methyl-4-cyano-2-nitrobenzene with a melting point of 105° to 106° C.

Workup

  1. customequipped with a drip funnel
  2. stirringthe mixture was agitated at 0° C. for two hours
  3. additionthe reaction mixture was then poured onto 400 parts by weight of ice
  4. filtrationThe precipitate was recovered by filtration
  5. washthoroughly washed with water
  6. customdried in air

Sources & evidence

ORD record
ord-16349aa360c44e4dba0d13a39b394ebb
Source dataset
uspto-grants-1985_04
Patent number
US04512929

Reaction notes

Loading…