2-Nitropropane → Methyl 4-methyl-4-nitropentanoate

HRID 432988Notes

Reaction equation

HRID 432988 reaction equation
[N+:1]([CH:4]([CH3:6])[CH3:5])([O-:3])=[O:2].[C:7]([O:11][CH3:12])(=[O:10])[CH:8]=[CH2:9].[F-].[K+]>C(O)C>[CH3:5][C:4]([N+:1]([O-:3])=[O:2])([CH3:6])[CH2:9][CH2:8][C:7]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 3

HCID 3982-NitropropaneHCID 7294Methyl AcrylateHCID 522689Potassium Fluoride

Product 1

HCID 247995Methyl 4-methyl-4-nitropentanoateYield 82.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Nitropropane (25 g, 0.28 mol) was dissolved in ethanol (140 ml) and methyl acrylate (25.3 ml, 0.28 mol) and potassium fluoride (1.63 g, 0.028 mol) were added. The mixture was refluxed under heating for 4 h. After cooling, ethanol was evaporated by concentration under reduced pressure, and the residue was extracted with ethyl acetate (100 ml) and water (50 ml). Ethyl acetate was evaporated under reduced pressure to give the objective compound (40.6 g, yield 82.5%).

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 4 h
  3. temperatureAfter cooling
  4. customethanol was evaporated by concentration under reduced pressure
  5. extractionthe residue was extracted with ethyl acetate (100 ml) and water (50 ml)
  6. customEthyl acetate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ccc948abd5844586878f36c5743c00a8
Source dataset
uspto-grants-2003_12
Patent number
US06664412B2

Reaction notes

Loading…