Hydrochloric Acid → (1E)-1-(2,4-Difluorophenyl)-1,2-propanedione 1-oxime

HRID 433024Notes

Reaction equation

HRID 433024 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10](=[O:12])[CH3:11].[N:13](OCCC(C)C)=[O:14].Cl>CC1CCCCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1/[C:9](=[N:13]\[OH:14])/[C:10](=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 27348812,4-Difluorophenylacetone

Product 1

HCID 18760905(1E)-1-(2,4-Difluorophenyl)-1,2-propanedione 1-oximeYield 92.2%

Reagents, catalysts & solvents 1

HCID 7962MethylcyclohexaneSolvent

Conditions

Temperature
32.5 °C

Procedure

A solution of 140.2 g (0.80 mol) of 1-(2,4-difluoro-phenyl)-propane-2-one in 550 g of methylcyclohexane is warmed up to 30-35° C. Over a period of 2 hours 96.6 g (0.80 mol) of isoamyl nitrite is added while a slow stream of dry hydrogen chloride is fed subsurface into the reactor. Following the end of the addition the batch is stirred for 15 minutes at 30-35° C. before the suspension is cooled to 0° C. The product is isolated by filtration and the filter cake is washed with 150 g of methylcyclohexane at 0° C.: 146.9 g of (E)-1-(2,4-difluoro-phenyl)-propane-1,2-dione 1-oxime (mp. 133-135° C.) are obtained in 89.5% yield.

Workup

  1. additionthe end of the addition the batch
  2. temperatureis cooled to 0° C
  3. customThe product is isolated by filtration
  4. washthe filter cake is washed with 150 g of methylcyclohexane at 0° C.

Sources & evidence

ORD record
ord-db08a7cce8b74e5d88a3d99ebc1bcc34
Source dataset
uspto-grants-2003_12
Patent number
US06664422B1

Reaction notes

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