Hydrochloric Acid → 1,6-Dichlorohexan-2-one

HRID 1973564Notes

Reaction equation

HRID 1973564 reaction equation
[N+](=C)=[N-].N([CH2:6]NC(N)=O)=O.[OH-:11].[K+].Cl[CH2:14][CH2:15][CH2:16][CH2:17][C:18]([Cl:20])=O.[ClH:21]>CCOCC>[Cl:21][CH2:6][C:14](=[O:11])[CH2:15][CH2:16][CH2:17][CH2:18][Cl:20]

Participants

7

Reactant 5

HCID 313Hydrochloric Acid2×HCID 9550DiazomethaneHCID 14797Potassium HydroxideHCID 740895-Chlorovaleryl chlorideHCID 104823Urea, (nitrosomethyl)-

Product 1

HCID 128060181,6-Dichlorohexan-2-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To an ethereal solution of diazomethane (prepared by the reaction of 90 parts of N-nitrosomethylurea with 175 parts by volume of 45% aqueous potassium hydroxide in 375 parts by volume of ether) is added dropwise, at 0° C., 50 parts of 5-chlorovaleryl chloride and the resulting reaction mixture is allowed to warm to room temperature with stirring, then stirred for an additional 16 hours. A saturated solution of dry hydrogen chloride in ether is then added portionwise to the point at which the solution becomes colorless. This solution containing the diazoketone and hydrogen chloride is stirred at room temperature for about 16 hours, then is washed successively with water, saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. Removal of the solvent by distillation under reduced pressure affords 1,6-dichloro-2-hexanone.

Workup

  1. additionis added dropwise, at 0° C.
  2. stirringstirred for an additional 16 hours
  3. stirringis stirred at room temperature for about 16 hours
  4. washis washed successively with water, saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customRemoval of the solvent
  7. distillationby distillation under reduced pressure

Sources & evidence

ORD record
ord-60ef9ed9581d4a51895375a46ddb4dc2
Source dataset
uspto-grants-1976_12
Patent number
US03997588

Reaction notes

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