Nitric Acid → 5-Methyl-6-nitro-1,3-benzodioxole

HRID 1244206

Reaction equation

HRID 1244206 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH3:10])=[CH:4][C:3]=2[O:2]1.[N+:11]([O-])([OH:13])=[O:12]>C(O)(=O)C>[N+:11]([C:6]1[CH:7]=[C:8]2[O:9][CH2:1][O:2][C:3]2=[CH:4][C:5]=1[CH3:10])([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 815641,3-Benzodioxole, 5-methyl-

Product 1

HCID 45504615-Methyl-6-nitro-1,3-benzodioxoleYield 64.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 10 (19.0 g, 139.6 mmol) in acetic acid (180 mL) was added a solution of fuming HNO3 (10 mL) in acetic acid (70 mL) dropwise over 30 minutes. The mixture was stirred at ambient temperature for 10 minutes, then poured into a beaker containing ice to give a crystalline precipitate, which was collected by vacuum filtration and washed with water to afford the crude product. Further purification via recrystallization from CH2Cl2/hexane gave the pure product (16.3 g, 64.4%).

Workup

  1. additionpoured into a beaker
  2. additioncontaining ice
  3. customto give a crystalline precipitate, which
  4. filtrationwas collected by vacuum filtration
  5. washwashed with water
  6. customto afford the crude product
  7. customFurther purification
  8. customvia recrystallization from CH2Cl2/hexane

Sources & evidence

ORD record
ord-6b5c397707b34e689a13265ae5d3d2b4
Source dataset
uspto-grants-2006_10
Patent number
US07122526B2

Linked notes

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