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

HRID 574899Notes

Reaction equation

HRID 574899 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). 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 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. temperatureThe solution was warmed up to room temperature
  2. temperatureThe mixture was heated
  3. temperatureto reflux overnight
  4. customThe reaction mixture was quenched by 0° C. solution of sodium acetate (25 g in 50 mL water)
  5. extractionThe aqueous layer was extracted with ether (3×200 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-466948b4c58d4be1bcfe62fa9af2136b
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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