Acetic Acid → 2,2-dimethyl-5,6-dinitro-1,3-benzodioxole

HRID 2248107Notes

Reaction equation

HRID 2248107 reaction equation
[N+:1]([O-:4])([OH:3])=O.C(O)(=O)C.[CH3:9][C:10]1([CH3:22])[O:14][C:13]2[CH:15]=[CH:16][C:17]([N+:19]([O-:21])=[O:20])=[CH:18][C:12]=2[O:11]1>O>[CH3:9][C:10]1([CH3:22])[O:11][C:12]2[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[C:16]([N+:1]([O-:4])=[O:3])=[CH:15][C:13]=2[O:14]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 2330662,2-Dimethyl-5-nitro-1,3-benzodioxole

Product 1

HCID 50472752,2-dimethyl-5,6-dinitro-1,3-benzodioxoleYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 90% (fuming) nitric acid (22 ml) and glacial acetic acid (11 ml) cooled at 12° C. was treated in portions with solid compound from Example 3B (5.4 g, 27.7 mmoles) so as to maintain the temperature of <17° C. After the addition, stirring was continued for 15 minutes, when the internal temperature began to fall. The mixture was diluted to 100 ml with water, the yellow solid filtered, washed with water, taken up in CH2Cl2, dried (Na2SO4) and evaporated to give 5.43 g (82%) of pure title compound.

Workup

  1. temperatureto maintain the temperature of <17° C
  2. additionAfter the addition
  3. filtrationthe yellow solid filtered
  4. washwashed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-a29cdd118e834e90807861c774570d23
Source dataset
uspto-grants-1991_08
Patent number
US05037983

Reaction notes

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