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

HRID 1164521

Reaction equation

HRID 1164521 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.[N+:15]([O-])([OH:17])=[O:16]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:7]=[C:6]([N+:15]([O-:17])=[O:16])[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 2

HCID 944Nitric AcidHCID 130971441,4-Dichloro-2-cyclohexylbenzene

Product 1

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

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

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-1f0da45e7bb24e9f84114a89d982f605
Source dataset
uspto-grants-1983_01
Patent number
US04370340

Linked notes

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