Sodium Carbonate → 4-Oxo-2-nonenal

HRID 546355Notes

Reaction equation

HRID 546355 reaction equation
[CH2:1]([C:6]1[O:7][CH:8]=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH3:5].ClC1C=CC=C(C(OO)=[O:19])C=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[O:19]=[C:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])/[CH:10]=[CH:9]/[CH:8]=[O:7]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 196022-PentylfuranHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 64455374-Oxo-2-nonenalYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.0 g (14.47 mmol) of 2-pentylfuran was dissolved in 60 ml of dichloromethane, and 3.84 g (14.47 mmol) of 65% m-chloroperbenzoic acid was added dropwise thereto with stirring under ice-cooling, followed by stirring for 1 hour at the same temperature. To the reaction solution was added saturated aqueous sodium carbonate and the mixture was extracted with dichloromethane. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and was then concentrated under reduced pressure to give 1.62 g of the title compound as a yellow oil (yield: 73%).

Workup

  1. temperaturecooling
  2. stirringby stirring for 1 hour at the same temperature
  3. extractionthe mixture was extracted with dichloromethane
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationwas then concentrated under reduced pressure

Sources & evidence

ORD record
ord-efd4299953bf4ed4b9c7d8ba225cc5fe
Source dataset
uspto-grants-2011_05
Patent number
US07935835B2

Reaction notes

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