Acetic Acid → 2,2-Dimethyl-5-nitro-1,3-benzodioxole

HRID 2248106Notes

Reaction equation

HRID 2248106 reaction equation
[N+:1]([O-:4])(O)=[O:2].C(O)(=O)C.[CH3:9][C:10]1([CH3:19])[O:14][C:13]2[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=2[O:11]1>O>[CH3:9][C:10]1([CH3:19])[O:11][C:12]2[CH:18]=[CH:17][C:16]([N+:1]([O-:4])=[O:2])=[CH:15][C:13]=2[O:14]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 2858692,2-Dimethyl-1,3-benzodioxole

Product 1

HCID 2330662,2-Dimethyl-5-nitro-1,3-benzodioxole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 70% (conc.) nitric acid (20 ml) and glacial acetic acid (10 ml) cooled at 12° C. was treated by drops with 5 g (33.3 mmole) of the compound of Example 3A at a rate to maintain the temperature at 15°-20° C. Stirring was continued for 15 minutes after addition, then the brown slurry was diluted to 100 ml with water and filtered. The solid was washed with water, taken up in CH2Cl2, dried (Na2SO4) and evaporated to 5.40 g (83%) of pure yellow mononitro title compound.

Workup

  1. temperatureto maintain the temperature at 15°-20° C
  2. additionafter addition
  3. filtrationfiltered
  4. washThe solid was washed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated to 5.40 g (83%) of pure yellow mononitro title compound

Sources & evidence

ORD record
ord-59ccbc6a7b29438d8b15da99e1c42378
Source dataset
uspto-grants-1991_08
Patent number
US05037983

Reaction notes

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