Nitric Acid → 1-(2,2-Dichlorocyclopropyl)-4-nitrobenzene

HRID 972884Notes

Reaction equation

HRID 972884 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1([Cl:15])[CH2:8][CH:7]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O.S(=O)(=O)(O)O>C(O)(=O)C>[Cl:5][C:6]1([Cl:15])[CH2:8][CH:7]1[C:9]1[CH:10]=[CH:11][C:12]([N+:1]([O-:4])=[O:2])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 1118Sulfuric AcidHCID 953491,1-Dichloro-2-phenylcyclopropane

Product 1

HCID 31271521-(2,2-Dichlorocyclopropyl)-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
4 °C

Procedure

Nitric acid (25 g.) was added during three hours to a mixture of (2,2-dichlorocyclopropyl)benzene (45 g.), water (13 g.), acetic acid (40 g.) and concentrated sulfuric acid (177 g.) with cooling (to 3-5° C.). The resulting mixture was quenched in a mixture of ice (400 g.) and chloroform (200 g.). The layers were separated and the aqueous layer was washed with chloroform (100 g.). The chloroform layers were combined and washed with aqueous sodium carbonate (5%, 300 ml.). The sodium carbonate layer was backwashed with chloroform (75 g.). The combined chloroform extracts were dried, fitered and concentrated, affording p-(2,2-dichlorocyclopropyl)nitrobenzene mixed with the ortho isomer (57 g.).

Workup

  1. customThe resulting mixture was quenched in a mixture of ice (400 g.) and chloroform (200 g.)
  2. customThe layers were separated
  3. washthe aqueous layer was washed with chloroform (100 g.)
  4. washwashed with aqueous sodium carbonate (5%, 300 ml.)
  5. dry with materialThe combined chloroform extracts were dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-250df96471cb4983aa8c537adc700a64
Source dataset
uspto-grants-1977_10
Patent number
US04053636

Reaction notes

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