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

HRID 2257089Notes

Reaction equation

HRID 2257089 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 15a were introduced, and a mixture of 250 ml of 100% strength by weight nitric acid and 350 ml of concentrated sulphuric acid were added dropwise, with stirring. The mixture was stirred for 2 hours at 55° C. The batch was then allowed to cool and poured into ice-water. The product was extracted using methylene chloride, and the methylene chloride phase was washed until neutral using sodium hydrogencarbonate solution, dried and freed from readily volatile components on a rotary evaporator. The yield was 339 g (=94% of theory), and the melting point was 101° to 103° C.

Workup

  1. additionwere added dropwise
  2. stirringThe mixture was stirred for 2 hours at 55° C
  3. temperatureto cool
  4. extractionThe product was extracted
  5. washthe methylene chloride phase was washed
  6. customdried
  7. customfreed from readily volatile components on a rotary evaporator

Sources & evidence

ORD record
ord-77ec0aa32e664646bbe35cb07ac84eeb
Source dataset
uspto-grants-1997_08
Patent number
US05656649

Reaction notes

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