Dimethylformamide → 2-Chlorocyclohex-1-enecarbaldehyde

HRID 2391081Notes

Reaction equation

HRID 2391081 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN([CH:11]=[O:12])C.P(Cl)(Cl)([Cl:15])=O.[OH-].[Na+]>C1(C)C=CC=CC=1.O>[Cl:15][C:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C:2]=1[CH:11]=[O:12]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7967CyclohexanoneHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychloride

Product 1

HCID 118048922-Chlorocyclohex-1-enecarbaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of cyclohexanone (1.34 g, 13.6 mmol) in toluene at room temperature was added DMF (1.58 mL, 20.5 mmol) and phosphorus oxychloride (1.88 mL, 20.5 mmol). The reaction was stirred overnight at room temperature, and then diluted with H2O and stirred for 30 minutes. 4N Aqueous NaOH (10 mL) was added, and the mixture was extracted with EtOAc. The combined organic layers were washed with saturated aqueous NH4Cl, dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

  1. stirringstirred for 30 minutes
  2. extractionthe mixture was extracted with EtOAc
  3. washThe combined organic layers were washed with saturated aqueous NH4Cl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9016d4d7ec9a4de5a8e51b178bfcceae
Source dataset
uspto-grants-2012_09
Patent number
US08273780B2

Reaction notes

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