Nitric Acid → HCID 70379756, compound

HRID 231370Notes

Reaction equation

HRID 231370 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH:12]([F:17])[C:13]([F:16])([F:15])[F:14])=[CH:7][CH:6]=1)(=O)C.[N+:18]([O-])([OH:20])=[O:19]>S(=O)(=O)(O)O>[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH:12]([F:17])[C:13]([F:16])([F:15])[F:14])=[CH:7][C:6]=1[N+:18]([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 70379591HCID 70379591, compound

Product 1

HCID 70379756HCID 70379756, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

18.8 g (0.08 moles) 4-acetylaminotetrafluoroethoxybenzene of Step 1 are dissolved, accompanied by ice cooling at 0° C., in 150 ml concentrated sulfuric acid. Nitration is carried out at the same temperature with a mixture of 10.3 ml (0.15 moles) concentrated nitric acid (d=1.4 g/ml) and 10 ml concentrated sulfuric acid. After standing overnight this mixture is poured onto approximately 500 g ice. A viscous oil precipitates. The oily phase is decanted and repeatedly washed with water. The oil is made to solidify by means of cooling and scraping. It is, according to DC, a mixture of acetylaminonitro- and aminonitro-compounds. It is then saponified by means of dissolving and boiling, with reflux, with methanol and concentrated hydrochloric acid and then neutralized with ammonia. The 4-amino-3-nitrotetrafluoroethoxybenzene precipitates. Yellow crystals with a melting point of 78° C. were obtained.

Workup

  1. customA viscous oil precipitates
  2. customThe oily phase is decanted
  3. washrepeatedly washed with water
  4. temperatureof cooling
  5. additiona mixture of acetylaminonitro- and aminonitro-compounds
  6. dissolutionof dissolving
  7. temperaturewith reflux, with methanol and concentrated hydrochloric acid
  8. customThe 4-amino-3-nitrotetrafluoroethoxybenzene precipitates
  9. customYellow crystals with a melting point of 78° C. were obtained

Sources & evidence

ORD record
ord-50225ce9db1c45a2be7310913dd0eab7
Source dataset
uspto-grants-1989_07
Patent number
US04845294

Reaction notes

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