Nitric Acid → HCID 19754703, compound

HRID 1588779Notes

Reaction equation

HRID 1588779 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[N+:14]([O-])([OH:16])=[O:15]>OS(O)(=O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[C:4]([N+:14]([O-:16])=[O:15])[CH:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 2371751-chloro-4-cyclohexylbenzene

Product 1

HCID 19754703HCID 19754703, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To 1-chloro-4-cyclohexylbenzene (1.7 g) in H2SO4 (10 mL) at 20° C. added HNO3 (2.5 g) in H2SO4 (10 mL) maintaining the temperature below 30° C. The mixture was allowed to stir for 1 h and then partitioned between CH2Cl2 and water. The CH2Cl2 layer was washed well with a saturated NaHCO3 solution, dried (MgSO4), and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 5% EtOAc/hexanes to give 5-chloro-2-cyclohexyl-1-nitrobenzene. This compound was then reduced with iron powder as described above to yield the desired compound.

Workup

  1. temperaturemaintaining the temperature below 30° C
  2. custompartitioned between CH2Cl2 and water
  3. washThe CH2Cl2 layer was washed well with a saturated NaHCO3 solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel eluting with 5% EtOAc/hexanes

Sources & evidence

ORD record
ord-f5813778e17149e1b1f2a716d2af2e65
Source dataset
uspto-grants-1993_06
Patent number
US05223526

Reaction notes

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