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

HRID 1417235Notes

Reaction equation

HRID 1417235 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

Conditions

Temperature
55 °C

Procedure

A mixture of 250 ml of 100% strength by weight nitric acid and 350 ml of concentrated sulphuric acid was added dropwise to an initial charge of 317 g of the product from Example 15a. The mixture was stirred at 55° C. for 2 hours. 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) and the melting point was 101° to 103° C.

Workup

  1. additionwas added dropwise to
  2. temperatureThe mixture was then cooled
  3. extractionThe product was extracted with methylene chloride
  4. washwashed until neutral with sodium hydrogen carbonate solution
  5. customdried
  6. customfreed on a rotary evaporator from readily volatile constituents

Sources & evidence

ORD record
ord-ce9987e78dcd4144803be821fbb8f271
Source dataset
uspto-grants-1999_03
Patent number
US05877195

Reaction notes

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