Nitromethane → Tert-butoxy-2-(2-nitrovinyl)benzene

HRID 1048101Notes

Reaction equation

HRID 1048101 reaction equation
[C:1]([O:5][C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].[N+:14]([CH3:17])([O-:16])=[O:15].Cl.CN.C([O-])(=O)C.[Na+]>ClCCl.O>[C:1]([O:5][C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH:8]=[CH:17][N+:14]([O-:16])=[O:15])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6375NitromethaneHCID 517045Sodium AcetateHCID 6364545Methylamine hydrochlorideHCID 149555262-tert-Butoxybenzaldehyde

Product 1

HCID 67080588Tert-butoxy-2-(2-nitrovinyl)benzeneYield 103.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

2-tert-Butoxybenzaldehyde (550 mg, 3.09 mmol) was treated with nitromethane (1167 μL, 21.6 mmol) at ambient temperature in a flask. Solid methylamine hydrochloride (133 mg, 1.98 mmol) and sodium acetate (162 mg, 1.98 mmol) were added and the colorless reaction mixture was stirred rapidly at ambient temperature. After 30 minutes, the reaction mixture started to turn yellow. After 16 hours, the reaction was very yellow and precipitate has formed. Water (20 ml) and dichloromethane (40 ml) were added and the layers partitioned. The dichloromethane layer was dried with sodium sulfate, filtered, and concentrated to provide the title compound (705 mg, 3.19 mmol, 103% yield) as a yellow oil.

Workup

  1. waitAfter 16 hours
  2. customprecipitate has formed
  3. customthe layers partitioned
  4. dry with materialThe dichloromethane layer was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8fe5e767b4864d2e8159f21da8e12d43
Source dataset
uspto-grants-2013_10
Patent number
US08569522B2

Reaction notes

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