Dimethylformamide → HCID 13096046, compound

HRID 2243181Notes

Reaction equation

HRID 2243181 reaction equation
CN([CH:4]=[O:5])C.P(Cl)(Cl)([Cl:8])=O.[CH3:11][CH:12]1[CH2:17][CH2:16][CH2:15][C:14](=O)[CH2:13]1.C([O-])(=O)C.[Na+]>ClC=C(Cl)Cl>[Cl:8][C:14]1[CH2:13][CH:12]([CH3:11])[CH2:17][CH2:16][C:15]=1[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 115673-MethylcyclohexanoneHCID 24813Phosphorus oxychlorideHCID 517045Sodium Acetate

Product 1

HCID 13096046HCID 13096046, compoundYield 108.7%

Reagents, catalysts & solvents 1

HCID 6575TrichloroethyleneSolvent2×

Procedure

To a solution of 446 μl (5.80 mmol) of DMF in 5 ml trichloroethylene were added 449 μl (4.90 mmol) of phosphorus oxychloride at 4° C. The mixture was then allowed to warm to RT and a solution of 500 mg (4.46 mmol) of 3-methyl-cyclohexanone in 5 ml trichloroethylene was added dropwise. After heating to 60° C. for 4 h, the reaction mixture was cooled to RT and 10 ml of a cold sodium acetate solution were added. The organic layer was separated and the aqueous phase was extracted with dichloromethane. The combined organic layers were then washed with brine, dried (MgSO4) and concentrated to yield 769 mg of crude 2-chloro-4-methyl-cyclohex-1-enecarbaldehyde (containing 10% of 2-chloro-6-methyl-cyclohex-1-enecarbaldehyde) as a light yellow oil.

Workup

  1. temperatureAfter heating to 60° C. for 4 h
  2. temperaturethe reaction mixture was cooled to RT
  3. customThe organic layer was separated
  4. extractionthe aqueous phase was extracted with dichloromethane
  5. washThe combined organic layers were then washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4014faac9bb6453f8f3c5d5e814f7a7b
Source dataset
uspto-grants-2010_03
Patent number
US07674815B2

Reaction notes

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