Nitric Acid → 5,6-Dinitro-1,3-benzodioxole

HRID 1476723Notes

Reaction equation

HRID 1476723 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=1)([O-:3])=[O:2].[N+:13]([O-])([OH:15])=[O:14]>>[N+:13]([C:12]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]2[O:10][CH2:9][O:8][C:7]=2[CH:11]=1)([O-:15])=[O:14]

Participants

3

Reactant 2

HCID 944Nitric Acid2×HCID 757981,3-Benzodioxole, 5-nitro-

Product 1

HCID 6113255,6-Dinitro-1,3-benzodioxole

Procedure

Compound 5-nitrobenzo[d][1,3]dioxole (5.0 g, 30 mmol) was added in one portion to a solution of fuming HNO3 and con. HNO3 (V/V=1/1, 120 mL) at −10 to −5° C. The mixture was stirred for 3 h at this temperature and poured into ice/water, filtered to get compound 5,6-dinitrobenzo[d][1,3]dioxole (7.0 g, quantitative) as a yellow solid. The compound was used directly without purification. 1H NMR (DMSO-d6) δ 6.39 (s, 2H), 7.86 (s, 2H).

Workup

  1. customat −10 to −5° C
  2. filtrationfiltered

Sources & evidence

ORD record
ord-295d184fe0a0477fb27fdddf5407de34
Source dataset
uspto-grants-2016_08
Patent number
US09402832B2

Reaction notes

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