Nitric Acid → 1-tert-Butyl-4,5-dichloro-2-nitrobenzene

HRID 1415587Notes

Reaction equation

HRID 1415587 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:13][C:12]=1[Cl:21]>>[Cl:10][C:11]1[CH:16]=[C:15]([N+:1]([O-:4])=[O:2])[C:14]([C:17]([CH3:19])([CH3:18])[CH3:20])=[CH:13][C:12]=1[Cl:21]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 21311711HCID 21311711, compound

Product 1

HCID 214832231-tert-Butyl-4,5-dichloro-2-nitrobenzene

Procedure

To a stirred and cooled (-5° C) mixture of 325 parts of nitric acid and 975 parts of a concentrated sulfuric acid solution are added dropwise 220 parts of 1,2-dichloro-4-(1,1-dimethylethyl)benzene. Upon completion, stirring is continued for 30 minutes at 5° C. The reaction mixture is poured onto water: the product precipitates as an oil. The supernatant aqueous water: is decanted and the residual oil is extracted with trichloromethane. The extract is washed with water, dried, filtered and evaporated. The residue is crystallized from 2-propanol. The product is filtered off and recrystallized from 2-propanol, yielding 34.5 parts of 1,2-dichloro-4-(1,1-dimethylethyl)-5-nitrobenzene; mp. 80° C.

Workup

  1. temperaturecooled
  2. stirringUpon completion, stirring
  3. additionThe reaction mixture is poured onto water
  4. customthe product precipitates as an oil
  5. customThe supernatant aqueous water: is decanted
  6. extractionthe residual oil is extracted with trichloromethane
  7. washThe extract is washed with water
  8. customdried
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue is crystallized from 2-propanol
  12. filtrationThe product is filtered off
  13. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-2725b4ccc3124f8aa3a503aa2b1cf420
Source dataset
uspto-grants-1977_01
Patent number
US04005218

Reaction notes

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