HCID 70379608, compound → HCID 86743225, compound

HRID 231367Notes

Reaction equation

HRID 231367 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH:11]([F:16])[C:12]([F:15])([F:14])[F:13])([O-:3])=[O:2].[N+:17](C1C=CC(OC(F)C(F)(F)F)=CC=1)([O-:19])=[O:18]>S(=O)(=O)(O)O.[N+]([O-])(O)=O>[N+:1]([C:4]1[CH:9]=[C:8]([N+:17]([O-:19])=[O:18])[CH:7]=[CH:6][C:5]=1[O:10][CH:11]([F:16])[C:12]([F:14])([F:15])[F:13])([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 70379608HCID 70379608, compoundHCID 70379838HCID 70379838, compound

Product 1

HCID 86743225HCID 86743225, compound

Reagents, catalysts & solvents 2

HCID 944Nitric AcidSolventHCID 1118Sulfuric AcidSolvent2×

Procedure

6 g (0.025 moles) of 2-nitrotetrafluoroethoxybenzene or 4-nitrotetrafluoroethoxybenzene are dissolved in 20 ml concentrated sulfuric acid (density, d=1.84 g/ml) and nitrated at 5°-10° C. with a mixture of 1.2 ml nitric acid (d=1.5 g/ml) and 5 ml sulfuric acid (d=1.84 g/ml). After the addition of the nitrating acid, the aforesaid preparation is allowed to heat at room temperature. The preparation, after being left to stand overnight, is then poured onto ice water. The precipitated oil is separated by means of decanting and the aqueous phase is extracted three times with 50 ml ether. The ether extracts and the oil are then combined, washed with sodium bicarbonate solution so as to be acid-free and dried over calcium chloride. After distilling the solvent, 6.6 g (93% of the theoretical yield) dinitro compound (from the 2-nitrotetrafluoroethoxybenzene) or 6.7 g (94% of the theoretical yield) dinitrotetrafluoroethoxybenzene (from the 4-nitrotetrafluoroethoxybenzene) is obtained. The dinitro compound was further processed directly in the following step without further purification.

Workup

  1. additionAfter the addition of the nitrating acid
  2. customthe aforesaid preparation
  3. customThe preparation
  4. waitafter being left
  5. additionis then poured onto ice water
  6. customThe precipitated oil is separated by means
  7. customof decanting
  8. extractionthe aqueous phase is extracted three times with 50 ml ether
  9. washwashed with sodium bicarbonate solution so as
  10. dry with materialdried over calcium chloride
  11. distillationAfter distilling the solvent, 6.6 g (93% of the

Sources & evidence

ORD record
ord-4e1f3003f31c439db1fbe2eca3c72602
Source dataset
uspto-grants-1989_07
Patent number
US04845294

Reaction notes

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