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

HRID 1973428Notes

Reaction equation

HRID 1973428 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH2:5]1[O:13][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6]1>O>[N+:1]([C:10]1[CH:11]=[CH:12][C:7]2[O:6][CH2:5][O:13][C:8]=2[CH:9]=1)([O-:4])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 92291,3-Benzodioxole

Product 1

HCID 757981,3-Benzodioxole, 5-nitro-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To 150 mls. of concentrated nitric acid cooled to and maintained at 0°C. is added 100 gms. of methylenedioxybenzene dropwise with vigorous stirring. At the end of the addition, the reaction mixture is diluted with several volumes of water, the precipitated solids collected by vacuum filtration and washed with several portions of water. Recrystallization of the crude solids from methanol provided 1-nitro-3,4-methylenedioxybenzene, m.p. 130°-141°C.

Workup

  1. additionis added 100 gms
  2. additionAt the end of the addition
  3. filtrationthe precipitated solids collected by vacuum filtration
  4. washwashed with several portions of water
  5. customRecrystallization of the crude solids from methanol

Sources & evidence

ORD record
ord-c00c1e68aac74ad8af2e820532177dd1
Source dataset
uspto-grants-1976_12
Patent number
US03997564

Reaction notes

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