Nitromethane → HCID 53887294, compound

HRID 1893526Notes

Reaction equation

HRID 1893526 reaction equation
[C:1]1([CH3:9])[C:2]([CH:7]=O)=[CH:3][CH:4]=[CH:5][CH:6]=1.C([O-])(=O)C.[NH4+].[N+:15]([CH3:18])([O-:17])=[O:16]>C(O)(=O)C.O>[CH3:9][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[CH:18][N+:15]([O-:17])=[O:16]

Participants

6

Reactant 3

HCID 6375NitromethaneHCID 107222-MethylbenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 53887294HCID 53887294, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

Ortho-tolualdehyde (10.00 g, 83.23 mmol) was dissolved in acetic acid (50 ml), ammonium acetate (6.93 g, 89.89 mmol) and nitromethane (7 ml, 129 mmol) were added, and the mixture was stirred at 110° C. for 8 hr and stood at room temperature overnight. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure to give the title compound (12.71 g, yield 94%) as a bistered oil.

Workup

  1. waitstood at room temperature overnight
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe insoluble material was filtered off
  6. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a9651f6e206145828a5228263c3f4dc1
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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