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

HRID 1744016Notes

Reaction equation

HRID 1744016 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-ed7242b8336f4b82bc5bf2b569ad81d8
Source dataset
uspto-grants-2006_03
Patent number
US07012152B2

Reaction notes

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