2-Nitropropane → 4-Methyl-4-nitrovaleronitrile

HRID 1744011Notes

Reaction equation

HRID 1744011 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[N+:5]([CH:8]([CH3:10])[CH3:9])([O-:7])=[O:6].[OH-].[Na+]>[Cl-].C([N+](C)(C)C)CCCCCCCCCCCCCCC>[CH3:9][C:8]([N+:5]([O-:7])=[O:6])([CH3:10])[CH2:3][CH2:2][C:1]#[N:4]

Participants

5

Reactant 3

HCID 3982-NitropropaneHCID 7855AcrylonitrileHCID 14798Sodium Hydroxide

Product 1

HCID 38791404-Methyl-4-nitrovaleronitrile

Reagents, catalysts & solvents 1

HCID 8154Hexadecyltrimethylammonium chlorideCatalyst

Procedure

(vii-1) Acrylonitrile and 2-nitropropane are reacted in the presence of hexadecyltrimethyl ammonium chloride in an aqueous alkali solvent such as aqueous sodium hydroxide solution and the like. Then, the reaction mixture is extracted to give 4-methyl-4-nitrovaleronitrile (European Journal of Organic Chemistry (1998), (2), 355–357). The obtained 4-methyl-4-nitrovaleronitrile can be isolated and/or purified by a conventional method, such as crystallization, chromatography and the like, but generally, can be used in the next step without isolation and/or purification.

Workup

  1. extractionThen, the reaction mixture is extracted

Sources & evidence

ORD record
ord-07d62603c1ef42939130f0e4eab6b31b
Source dataset
uspto-grants-2006_03
Patent number
US07012152B2

Reaction notes

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