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

HRID 858950Notes

Reaction equation

HRID 858950 reaction equation
[F-].[K+].[N+:3]([CH:6]([CH3:8])[CH3:7])([O-:5])=[O:4].[C:9]([O:13][CH3:14])(=[O:12])[CH:10]=[CH2:11]>C(O)C>[CH3:7][C:6]([N+:3]([O-:5])=[O:4])([CH3:8])[CH2:11][CH2:10][C:9]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 3

HCID 3982-NitropropaneHCID 7294Methyl AcrylateHCID 522689Potassium Fluoride

Product 1

HCID 247995Methyl 4-methyl-4-nitropentanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A catalytic amount of potassium fluoride is added to 2-nitropropane and methyl acrylate, and the mixture is refluxed under heating in a suitable solvent such as ethanol and the like. The reaction mixture is concentrated (or evaporated) and extracted to give methyl 4-methyl-4-nitropentanoate (Bulletin of the Chemical Society of Japan 1966, 39 (11), 2549–2551). The obtained methyl 4-methyl-4-nitropentanoate can be isolated and/or purified by a conventional method, such as distillation, chromatography and the like, but generally, can be used in the next step without isolation and/or purification.

Workup

  1. temperaturethe mixture is refluxed
  2. concentrationThe reaction mixture is concentrated
  3. custom(or evaporated)
  4. extractionextracted

Sources & evidence

ORD record
ord-6553fa9a989146a6afb9e100512da13e
Source dataset
uspto-grants-2006_12
Patent number
US07148371B2

Reaction notes

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