Hydrochloric Acid → 2-Octanone, 1,1,1-trifluoro-

HRID 893537Notes

Reaction equation

HRID 893537 reaction equation
[Mg].[CH2:2](Br)[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[F:9][C:10]([F:15])([F:14])[C:11](O)=[O:12].Cl>CCOCC>[F:9][C:10]([F:15])([F:14])[C:11](=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 81011-BromohexaneHCID 5462224Magnesium

Product 1

HCID 959112-Octanone, 1,1,1-trifluoro-Yield 54%

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 59.4 g (360 mM) of hexyl 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 11.8 g of 1,1,1-trifluoro-2-octanone. Yield: 46%.

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-d3c46bc2e0d243acaee234f2c18376b5
Source dataset
uspto-grants-1992_06
Patent number
US05126071

Reaction notes

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