Dimethylformamide → 2-chloro-4,4-diMethylcyclohex-1-enecarbaldehyde

HRID 1848828Notes

Reaction equation

HRID 1848828 reaction equation
CN(C)[CH:3]=[O:4].P(Cl)(Cl)([Cl:8])=O.[CH3:11][C:12]1([CH3:19])[CH2:17][CH2:16][CH2:15][C:14](=O)[CH2:13]1>ClCCl>[Cl:8][C:14]1[CH2:13][C:12]([CH3:19])([CH3:11])[CH2:17][CH2:16][C:15]=1[CH:3]=[O:4]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 76322Cyclohexanone, 3,3-dimethyl-

Product 1

HCID 866428722-chloro-4,4-diMethylcyclohex-1-enecarbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

Into a 250 mL round-bottomed flask was added N,N-dimethylformamide (3.5 mL) in dichloromethane (30 mL) to give a colorless solution. The mixture was cooled to −10° C., and phosphoryl trichloride (4 mL) was added dropwise. The solution was warmed up to room temperature, and 3,3-dimethylcyclohexanone (5.5 mL) was added slowly. The mixture was heated to reflux for overnight. The reaction mixture was quenched by 0° C. solution of sodium acetate (25 g in 50 mL water). The aqueous layer was extracted with ether (3×200 mL). The organic layers were combined, dried over Na2SO4, filtered, and dried under vacuum.

Workup

  1. customto give a colorless solution
  2. temperatureThe solution was warmed up to room temperature
  3. temperatureThe mixture was heated
  4. temperatureto reflux for overnight
  5. customThe reaction mixture was quenched by 0° C. solution of sodium acetate (25 g in 50 mL water)
  6. extractionThe aqueous layer was extracted with ether (3×200 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customdried under vacuum

Sources & evidence

ORD record
ord-8c190edbb2004b0cac520cc06cf0d8e3
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

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