Nitric Acid → 1,4-Dichloro-2-cyclohexyl-5-nitrobenzene

HRID 1903734

Reaction equation

HRID 1903734 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.S(=O)(=O)(O)O.[N+:20]([O-])([OH:22])=[O:21]>>[Cl:1][C:2]1[CH:7]=[C:6]([N+:20]([O-:22])=[O:21])[C:5]([Cl:8])=[CH:4][C:3]=1[CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 130971441,4-Dichloro-2-cyclohexylbenzene

Product 1

HCID 130971451,4-Dichloro-2-cyclohexyl-5-nitrobenzene

Procedure

To a solution of 1,4-dichloro-2-cyclohexylbenzene (12.0 g) in conc.sulfuric acid (15 ml) was added dropwise a mixture of nitric acid (d=1.42, 4 ml) and conc.sulfuric acid (6 ml) with stirring under ice-cooling. After the stirring was continued for 10 minutes, ice-water was added to the reaction mixture to give an oily residue, which was extracted with ether, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The resultant oily residue was distilled under reduced pressure to give 1,4-dichloro-2-cyclohexyl-5-nitrobenzene (10.0 g).

Workup

  1. temperaturecooling
  2. customto give an oily residue, which
  3. extractionwas extracted with ether
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. distillationThe resultant oily residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-2155171f4ae94ad5852a801fb143ba25
Source dataset
uspto-grants-1984_03
Patent number
US04438126

Linked notes

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