2-Nitropropane → 1-(2-methyl-2-nitropropyl)-4-nitrobenzene

HRID 1518642Notes

Reaction equation

HRID 1518642 reaction equation
[O-]CC.[Na+].Cl[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1.[N+:16]([CH:19]([CH3:21])[CH3:20])([O-:18])=[O:17]>C(O)C>[CH3:20][C:19]([N+:16]([O-:18])=[O:17])([CH3:21])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 3982-NitropropaneHCID 74824-Nitrobenzyl chlorideHCID 2723922Sodium ethoxide

Product 1

HCID 2280911-(2-methyl-2-nitropropyl)-4-nitrobenzeneYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of sodium ethoxide (3.5 g, 50 mmol) in ethanol (100 mL), 1-(chloromethyl)-4-nitrobenzene (8.6 g, 50 mmol) and 2-nitropropane (2.2 g, 250 mmol) were added at room temperature, and the mixture was heated under reflux for 18 hours. The reaction solution was filtered, concentrated under reduced pressure, and diluted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by flash column chromatography to obtain 1-(2-methyl-2-nitropropyl)-4-nitrobenzene (8.52 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. filtrationThe reaction solution was filtered
  4. concentrationconcentrated under reduced pressure
  5. additiondiluted with ethyl acetate
  6. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-2799d29ec068457bae7f754eba4eea3a
Source dataset
uspto-grants-2015_07
Patent number
US09072734B2

Reaction notes

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