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

HRID 745581Notes

Reaction equation

HRID 745581 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][C:6]1([CH3:15])[O:10][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[O:7]1>C(O)(=O)C>[CH3:5][C:6]1([CH3:15])[O:7][C:8]2[CH:14]=[CH:13][C:12]([N+:1]([O-:4])=[O:2])=[CH:11][C:9]=2[O:10]1

Participants

4

Reactant 2

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

Product 1

HCID 2330662,2-Dimethyl-5-nitro-1,3-benzodioxoleYield 33.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

24 ml of nitric acid (d=1.4) in 60 ml of glacial acetic acid were added dropwise at 15°-20° C. to 39.0 g of 2,2-dimethyl-1,3-benzodioxole in 200 ml of glacial acetic acid. After stirring at room temperature for 3 hours, the mixture was poured into ice/water and extracted twice with 1 l of methylene chloride. The organic phase was washed neutral with water, dried over sodium sulfate and evaporated in vacuo. The residue, recrystallized from methanol, gave 17.0 g (33.5% of theory) of 2,2-dimethyl-5-nitro-1,3-benzodioxole of melting point 88°-90° C.

Workup

  1. extractionextracted twice with 1 l of methylene chloride
  2. washThe organic phase was washed neutral with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue, recrystallized from methanol

Sources & evidence

ORD record
ord-67593faaab3e4a9b90f1d5aad111d973
Source dataset
uspto-grants-1986_07
Patent number
US04599347

Reaction notes

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