Dimethylformamide → HCID 86648181, compound

HRID 706948Notes

Reaction equation

HRID 706948 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][C:15](=O)[CH:14]=[CH:13]1>ClCCl>[Cl:8][C:15]1[CH:14]=[CH:13][C:12]([CH3:19])([CH3:11])[CH2:17][C:16]=1[CH:3]=[O:4]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 1368392-Cyclohexen-1-one, 4,4-dimethyl-

Product 1

HCID 86648181HCID 86648181, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

In a 250 mL round-bottomed flask was added N,N-dimethylformamide (3.5 mL) in dichloromethane (30 mL), and the mixture was cooled to −10° C. Phosphoryl trichloride (4 mL) was added dropwise, and the solution was warmed up to room temperature. 4,4-Dimethylcyclohex-2-enone (5.5 mL) was then added slowly, and the mixture was heated to reflux overnight. The reaction mixture was cooled and quenched with a 0° C. solution of sodium acetate (25 g in 50 mL water). The aqueous layer was extracted with diethyl ether (200 mL×3). The combined organic layers were dried over Na2SO4, filtered, and concentrated to give the product.

Workup

  1. temperaturethe solution was warmed up to room temperature
  2. temperaturethe mixture was heated
  3. temperatureto reflux overnight
  4. temperatureThe reaction mixture was cooled
  5. customquenched with a 0° C. solution of sodium acetate (25 g in 50 mL water)
  6. extractionThe aqueous layer was extracted with diethyl ether (200 mL×3)
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give the product

Sources & evidence

ORD record
ord-ee1d772c9194463aac4b9fdf56f31430
Source dataset
uspto-grants-2015_11
Patent number
US09174982B2

Reaction notes

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