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

HRID 858956Notes

Reaction equation

HRID 858956 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-c0e5ef6b8bb140c8944be579a7a62117
Source dataset
uspto-grants-2006_12
Patent number
US07148371B2

Reaction notes

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