Nitroethane → 5-(2-Nitro-1-propen-1-yl)-1,3-benzodioxole

HRID 551764Notes

Reaction equation

HRID 551764 reaction equation
[CH:1]1[C:6]([CH:7]=O)=[CH:5][C:4]2[O:9][CH2:10][O:11][C:3]=2[CH:2]=1.C([O-])(=O)C.[NH4+].[N+:17]([CH2:20][CH3:21])([O-:19])=[O:18]>>[N+:17]([C:20]([CH3:21])=[CH:7][C:6]1[CH:1]=[CH:2][C:3]2[O:11][CH2:10][O:9][C:4]=2[CH:5]=1)([O-:19])=[O:18]

Participants

4

Reactant 3

HCID 6587NitroethaneHCID 8438PiperonalHCID 517165Ammonium Acetate

Product 1

HCID 2263175-(2-Nitro-1-propen-1-yl)-1,3-benzodioxoleYield 40%

Conditions

Temperature
105 °C

Procedure

5.00 g (33.3 mmol) piperonal (Aldrich, Milwaukee, Wis.), 12.8 g (167 mmol) ammonium acetate (Fluke), and 50 g (670 Mmol) nitroethane, 98% (Aldrich) were combined in a 100 ml round bottom flask equipped with magnetic stirrer and nitrogen inlet. The reaction mixture was heated to 105° C. for 90 minutes and the solvent was removed under vacuum to give a dark yellow liquid which was recrystallized from cold methyl alcohol three times to give a yellow crystalline solid in 40% yield. 1H NMR spectra is shown in FIG. 1.

Workup

  1. customequipped with magnetic stirrer and nitrogen inlet
  2. customthe solvent was removed under vacuum
  3. customto give a dark yellow liquid which
  4. customwas recrystallized from cold methyl alcohol three times
  5. customto give a yellow crystalline solid in 40% yield

Sources & evidence

ORD record
ord-dc67cfc32bd144919155496923d8193b
Source dataset
uspto-grants-2011_05
Patent number
US07947849B2

Reaction notes

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