Nitric Acid → 1,3-Bis(2,6-dichloro-alpha,alpha,alpha-trifluoro-p-tolyloxy)-4-nitrobenzene

HRID 1979652Notes

Reaction equation

HRID 1979652 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[Cl:10][C:11]1[CH:16]=[C:15]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]3[CH:30]=[C:29]([Cl:31])[C:28]([C:32]([F:35])([F:34])[F:33])=[C:27]([Cl:36])[CH:26]=3)[CH:19]=2)[CH:14]=[C:13]([Cl:37])[C:12]=1[C:38]([F:41])([F:40])[F:39]>ClCCCl>[Cl:10][C:11]1[CH:16]=[C:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([N+:6]([O-:9])=[O:7])=[C:20]([O:24][C:25]3[CH:26]=[C:27]([Cl:36])[C:28]([C:32]([F:33])([F:34])[F:35])=[C:29]([Cl:31])[CH:30]=3)[CH:19]=2)[CH:14]=[C:13]([Cl:37])[C:12]=1[C:38]([F:41])([F:40])[F:39]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 867353071,3-Bis(2,6-dichloro-alpha,alpha,alpha-trifluoro-p-tolyloxy)-benzene

Product 1

HCID 867353061,3-Bis(2,6-dichloro-alpha,alpha,alpha-trifluoro-p-tolyloxy)-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A cooled mixture of concentrated sulfuric acid (6.5 ml.) and nitric acid (4.4 ml.) is added with stirring to an ice cold solution of 1,3-bis(2,6-dichloro-α,α,α-trifluoro-p-tolyloxy)-benzene (11.1 g. 0.021 mol) in 1,2-dichlorethane (30 ml.). After 30 minutes at room temperature, the phases are allowed to separate and the organic phase washed twice with water. Benzene (200 ml.) is added and the solution washed twice with dilute sodium carbonate solution, dried, filtered through activated silica gel (~25 g.), and the solvents removed. The residual crystals are triturated with pentane, filtered, and dried to obtain 1,3-bis(2,6-dichloro-α,α,α-trifluoro-p-tolyloxy)-4-nitrobenzene (9.9 g., 82%) m.p. 137.5°-140.5° C., 90% pure.

Workup

  1. additionis added
  2. customto separate
  3. washthe organic phase washed twice with water
  4. additionBenzene (200 ml.) is added
  5. washthe solution washed twice with dilute sodium carbonate solution
  6. customdried
  7. filtrationfiltered through activated silica gel (~25 g.)
  8. customthe solvents removed
  9. customThe residual crystals are triturated with pentane
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-36fd27cd16804cca8539f9a7c25c6fd3
Source dataset
uspto-grants-1984_11
Patent number
USRE031731

Reaction notes

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