Hydrochloric Acid → 1,1,1-Trifluoro-2-hexanone

HRID 893534Notes

Reaction equation

HRID 893534 reaction equation
[Mg].[CH2:2](Br)[CH2:3][CH2:4][CH3:5].[F:7][C:8]([F:13])([F:12])[C:9](O)=[O:10].Cl>CCOCC>[F:7][C:8]([F:13])([F:12])[C:9](=[O:10])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 8002Butyl bromideHCID 5462224Magnesium

Product 1

HCID 2382921,1,1-Trifluoro-2-hexanoneYield 51.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

In a nitrogen atmosphere, 9.12 g (380 mM) of magnesium into 120 ml of ether, and 49.32 g (360 mM) of butyl bromide dissolved in 30 ml of ether was added thereto, followed by 1.5 hours of heat refluxing. After cooling by standing and with ice, 13.68 g (120 mM) of trifluoroacetic acid dissolved in 30 ml of ether was added. After being stirred for 7 hours under cooling with ice, the system was subjected to hydrolysis with addition of hydrochloric acid, followed by extraction with ether and drying of the resultant ether layer with anhydrous sodium sulfate. The dried product was distilled under normal pressure to obtain 9.46 g of 1,1,1-trifluoro-2-hexanone. Yield: 47%.

Workup

  1. additionwas added
  2. temperatureof heat
  3. temperaturerefluxing
  4. temperatureAfter cooling
  5. additionwas added
  6. temperatureunder cooling with ice
  7. extractionfollowed by extraction with ether
  8. dry with materialdrying of the resultant ether layer with anhydrous sodium sulfate
  9. distillationThe dried product was distilled under normal pressure

Sources & evidence

ORD record
ord-e1c7157d4e1c45028c7d5f21ea1dc8af
Source dataset
uspto-grants-1992_06
Patent number
US05126071

Reaction notes

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