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

HRID 27314Notes

Reaction equation

HRID 27314 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[C:18]([Cl:26])[CH:17]=3)[CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:27]([F:30])([F:29])[F:28].[N+:31]([O-])([OH:33])=[O:32].S(=O)(=O)(O)O.CCCCCC>O.C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:31]([O-:33])=[O:32])=[C:11]([O:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:23])([F:24])[F:25])=[C:18]([Cl:26])[CH:17]=3)[CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:27]([F:30])([F:28])[F:29]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 8058HexaneHCID 867353051,3-Bis(2-chloro-alpha,alpha,alpha-trifluoro-p-tolyloxy)benzene

Product 1

HCID 867353041,3-Bis(2-chloro-alpha,alpha,alpha-trifluoro-p-tolyloxy)-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 22272175Benzene--water (1/1)Solvent

Procedure

1,3-Bis(2-chloro-α,α,α-trifluoro-p-tolyloxy)benzene (12 g. 0.0255 mole) is added to a mixture of concentrated nitric acid (12 g.) and sulfuric acid (15 g.) at 5° C. The temperature is then allowed to rise to 25°-30° C. with manual stirring and mild ice bath cooling and after 10-20 minutes, the oil solidifies. The mixture is taken up in water/benzene (400 ml)/hexane (400 ml) and the organic phase is washed with water, dried, filtered through activated silica gel (~20 g.), and the solvents removed. The residue is recrystallized from isopropanol to give 1,3-bis(2-chloro-α,α,α-trifluoro-p-tolyloxy)-4-nitrobenzene, (7.4 g. 56%) m.p. 110°-111.5° C.

Workup

  1. customto rise to 25°-30° C. with manual
  2. temperaturemild ice bath cooling and after 10-20 minutes
  3. washthe organic phase is washed with water
  4. customdried
  5. filtrationfiltered through activated silica gel (~20 g.)
  6. customthe solvents removed
  7. customThe residue is recrystallized from isopropanol

Sources & evidence

ORD record
ord-4ae9ad4c84a74ddb99cfef1f5ccc5ab8
Source dataset
uspto-grants-1980_09
Patent number
US04220468

Reaction notes

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