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

HRID 1081294Notes

Reaction equation

HRID 1081294 reaction equation
[N+:1]([O-:4])([OH:3])=O.[N+:5]([C:8]1[CH:25]=[CH:24][C:11]2[O:12][C:13]([CH2:19][C:20]([F:23])([F:22])[F:21])([C:15]([F:18])([F:17])[F:16])[O:14][C:10]=2[CH:9]=1)([O-:7])=[O:6]>S(=O)(=O)(O)O>[N+:1]([C:25]1[C:8]([N+:5]([O-:7])=[O:6])=[CH:9][C:10]2[O:14][C:13]([CH2:19][C:20]([F:23])([F:21])[F:22])([C:15]([F:17])([F:16])[F:18])[O:12][C:11]=2[CH:24]=1)([O-:4])=[O:3]

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

A mixture of 250 ml of 100% strength by weight nitric acid and 350 ml of concentrated sulphuric acid was added dropwise with stirring to an initial charge of 317 g of the product from Example 15a. The mixture was stirred for 2 hours at 55° C. The mixture was then cooled and poured into ice-water. The product was extracted with methylene chloride, washed until neutral with sodium hydrogen carbonate solution, dried, and freed on a rotary evaporator from readily volatile constituents. The yield was 339 g (=94% of theory), the melting point was 101° to 103° C.

Workup

  1. additionwas added dropwise
  2. stirringThe mixture was stirred for 2 hours at 55° C
  3. temperatureThe mixture was then cooled
  4. extractionThe product was extracted with methylene chloride
  5. washwashed until neutral with sodium hydrogen carbonate solution
  6. customdried
  7. customfreed on a rotary evaporator from readily volatile constituents

Sources & evidence

ORD record
ord-0e60ad0849ee405a87c86c2dd4a42022
Source dataset
uspto-grants-1996_12
Patent number
US05585395

Reaction notes

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