Nitric Acid → 1,3-Benzodioxole, 5-nitro-

HRID 1903146Notes

Reaction equation

HRID 1903146 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[O:3][CH2:2]1.[N+:10]([O-])([OH:12])=[O:11]>C(O)(=O)C>[N+:10]([C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH2:2][O:3][C:4]=2[CH:9]=1)([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 92291,3-Benzodioxole

Product 1

HCID 757981,3-Benzodioxole, 5-nitro-Yield 90.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

12.2 g of 1,3-benzodioxole were placed in 75 ml of glacial acetic acid in a 250 ml sulfonation flask equipped with stirrer, thermometer and dropping funnel and then nitrated at 15°-25° C. by the dropwise addition of 9 ml of nitric acid (d=1.4) in 30 ml of glacial acetic acid. The mixture was stirred at room temperature overnight, the precipitated crystals were removed by filtration under suction, washed with water and recrystallized from alcohol. There were obtained 14.0 g of 5-nitro-1,3-benzodioxole of melting point 149°-150° C. and from the mother liquor an additional 2.0 g of melting point 148°-149° C. Total yield: 90.6% of theory.

Workup

  1. customequipped with stirrer
  2. customthe precipitated crystals were removed by filtration under suction
  3. washwashed with water
  4. customrecrystallized from alcohol

Sources & evidence

ORD record
ord-afc9d987fc6d431e8c91082c32f5b4dc
Source dataset
uspto-grants-1984_03
Patent number
US04435406

Reaction notes

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