Nitric Acid → BENZENEACETONITRILE, ?-(1-METHYLETHYL)-4-NITRO-

HRID 1106019Notes

Reaction equation

HRID 1106019 reaction equation
[N+:1]([O-:4])(O)=[O:2].[C:5]1([CH:11]([CH:14]([CH3:16])[CH3:15])[C:12]#[N:13])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>S(=O)(=O)(O)O>[N+:1]([C:8]1[CH:9]=[CH:10][C:5]([CH:11]([CH:14]([CH3:16])[CH3:15])[C:12]#[N:13])=[CH:6][CH:7]=1)([O-:4])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 2497223-methyl-2-phenylbutanenitrile

Product 1

HCID 3677245BENZENEACETONITRILE, ?-(1-METHYLETHYL)-4-NITRO-

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Into mixed acids (5 ml of 90% nitric acid and 60 ml of concentrated sulfuric acid), held at -2° to -3° with a dry-ice/acetone bath, was dripped 15.92 g of 2-phenyl-3-methylbutyronitrile, causing a very exothermic reaction during the 7-minutes addition period. After an additional 70 minutes at -5° to 0°, the dark reddish orange reaction mixture was poured into excess ice. The thick oil which formed was extracted into butyl chloride, and the butyl chloride extract washed twice each with water and saturated sodium bicarbonate solution. Drying (MgSO4) and evaporation of the butyl chloride solution provided an orange-yellow oil. Vacuum distillation gave 17.1 g of yellow oil, bp 118°-130°/(0.2-0.3 Torr). Crystallization from butyl chloride/hexane provided white 2-(4-nitrophenyl)-3-methylbutyronitrile of m.p. 69°-71°.

Workup

  1. customheld at -2° to -3° with a dry-ice/acetone bath
  2. customa very exothermic reaction
  3. additionduring the 7-minutes addition period
  4. additionthe dark reddish orange reaction mixture was poured into excess ice
  5. customThe thick oil which formed
  6. extractionwas extracted into butyl chloride
  7. extractionthe butyl chloride extract
  8. washwashed twice each with water and saturated sodium bicarbonate solution
  9. customDrying
  10. custom(MgSO4) and evaporation of the butyl chloride solution
  11. customprovided an orange-yellow oil
  12. distillationVacuum distillation

Sources & evidence

ORD record
ord-367951b977344b43b6d1d2c42595a6ef
Source dataset
uspto-grants-1982_01
Patent number
US04311696

Reaction notes

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