Ethyl Acrylate → Methyl 4-nitrononanoate

HRID 2296639Notes

Reaction equation

HRID 2296639 reaction equation
[C:1]([O:5][CH2:6]C)(=[O:4])[CH:2]=[CH2:3].[N+:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])([O-:10])=[O:9].C([O-])([O-])=O.[K+].[K+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].CCOCC>[N+:8]([CH:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:3][CH2:2][C:1]([O:5][CH3:6])=[O:4])([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 8821Ethyl AcrylateHCID 11430Potassium CarbonateHCID 125891-Nitrohexane

Product 1

HCID 10632556Methyl 4-nitrononanoate

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 3283Diethyl EtherSolvent

Procedure

A suspension of ethyl acrylate, 1-nitrohexane, K2CO3, and Aliquat 336 (6 drops) is sonicated for 5 h. To the reaction is added Et2O. The reaction mixture is filtered, extracted with brine, dried over Na2SO4 (anhydrous), filtered, and concentrated under reduced pressure to give a yellow liquid. The product is purified by column chromatography to give methyl 4-nitrononanoate.

Workup

  1. customis sonicated for 5 h
  2. filtrationThe reaction mixture is filtered
  3. extractionextracted with brine
  4. dry with materialdried over Na2SO4 (anhydrous)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a yellow liquid
  8. customThe product is purified by column chromatography

Sources & evidence

ORD record
ord-a7bd9cc6bcde4f2992d4d3bf87ddc8b3
Source dataset
uspto-grants-2002_12
Patent number
US06489323B1

Reaction notes

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