Nitric Acid → 5,6-Dinitro-2-(2,2,2-trifluoroethyl)-2-(trifluoromethyl)-1,3-benzodioxole

HRID 37573Notes

Reaction equation

HRID 37573 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]2[O:8][C:9]([CH2:15][C:16]([F:19])([F:18])[F:17])([C:11]([F:14])([F:13])[F:12])[O:10][C:6]=2[CH:5]=1)([O-:3])=[O:2].[N+:22]([O-])([OH:24])=[O:23]>S(=O)(=O)(O)O>[N+:1]([C:4]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][C:7]2[O:8][C:9]([CH2:15][C:16]([F:19])([F:18])[F:17])([C:11]([F:12])([F:13])[F:14])[O:10][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 538772305-Nitro-2-(2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole

Product 1

HCID 536607065,6-Dinitro-2-(2,2,2-trifluoroethyl)-2-(trifluoromethyl)-1,3-benzodioxole

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

317 g of the product of Example 27 were taken and a mixture of 250 ml of 100% by weight nitric acid and 350 ml of concentrated sulphuric acid was added dropwise, with stirring. The reaction mixture was stirred for 2 hours at 55° C. It was then left to cool and poured into ice-water. The product was extracted with methylene chloride, the extract was washed with sodium hydrogen-carbonate solution until the washings were neutral, and dried, and the readily volatile components were removed on a rotary evaporator. The yield was 339 g (=94% of theory) and the melting point was 101° to 103° C. The NMR spectra showed the following characteristic absorptions: 19F NMR: -60.9 and -86.5 ppm. 1H NMR: 3.18 ppm.

Workup

  1. additionwas added dropwise
  2. stirringThe reaction mixture was stirred for 2 hours at 55° C
  3. waitIt was then left
  4. temperatureto cool
  5. extractionThe product was extracted with methylene chloride
  6. washthe extract was washed with sodium hydrogen-carbonate solution until the washings
  7. customdried
  8. customthe readily volatile components were removed on a rotary evaporator

Sources & evidence

ORD record
ord-6749d7b9b96d42caaceeff9906e2b253
Source dataset
uspto-grants-1995_05
Patent number
US05420309

Reaction notes

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