Nitric Acid → HCID 57287217, compound

HRID 476816Notes

Reaction equation

HRID 476816 reaction equation
[F:1][CH:2]([O:7][C:8]1[CH:9]=[C:10]([CH3:14])[CH:11]=[CH:12][CH:13]=1)[C:3]([F:6])([F:5])[F:4].[N+:15]([O-])([OH:17])=[O:16].S(=O)(=O)(O)O>C(O)(=O)C>[N+:15]([C:13]1[CH:12]=[CH:11][C:10]([CH3:14])=[CH:9][C:8]=1[O:7][CH:2]([F:1])[C:3]([F:4])([F:5])[F:6])([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 56986549HCID 56986549, compound

Product 1

HCID 57287217HCID 57287217, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

20.8 g (0.10 moles) 3-tetrafluoroethoxytoluene is placed in 25 ml glacial acetic acid and nitrated at 5° C. with a mixture of 30 ml concentrated nitric acid and 35 ml concentrated sulfuric acid. The solution turns yellow as the nitrating acid is added dropwise. When the addition is terminated the cooling bath is removed and the solution is agitated for 31/2 hours at room temperature. The solution is then poured onto ice, the precipitated oil separated and the aqueous solution is extracted with ethyl acetate. After drying over sodium sulfate and distilling the solvent, a yellow oil remains in quantitative yield, which according to the NMR spectrum, involves the 4-nitro-3-tetrafluoroethoxytoluene.

Workup

  1. additionis added dropwise
  2. additionWhen the addition
  3. customis terminated the cooling bath
  4. customis removed
  5. additionThe solution is then poured onto ice
  6. customthe precipitated oil separated
  7. extractionthe aqueous solution is extracted with ethyl acetate
  8. dry with materialAfter drying over sodium sulfate
  9. distillationdistilling the solvent

Sources & evidence

ORD record
ord-f4225e53d58f4ec9876cebd50d7653cf
Source dataset
uspto-grants-1989_12
Patent number
US04886516

Reaction notes

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