Sulfuric Acid → 5-(Trifluoromethyl)cyclohexane-1,3-dione

HRID 2192582Notes

Reaction equation

HRID 2192582 reaction equation
COC([CH:5]1[C:10]([O-:11])=[CH:9][C:8](=[O:12])[CH2:7][CH:6]1[C:13]([F:16])([F:15])[F:14])=O.[Na+].[OH-].[Na+].S(=O)(=O)(O)O>>[F:14][C:13]([F:15])([F:16])[CH:6]1[CH2:7][C:8](=[O:12])[CH2:9][C:10](=[O:11])[CH2:5]1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 59226399Sodium 6-(Methoxycarbonyl)-3-oxo-5-(trifluoromethyl)cyclohex-1-enolate

Product 1

HCID 592265745-(Trifluoromethyl)cyclohexane-1,3-dione

Procedure

Sodium 6-(Methoxycarbonyl)-3-oxo-5-(trifluoromethyl)cyclohex-1-enolate (1.0 eq) was dissolved in 1M NaOH (1.0 eq), and the mixture refluxed for 1 h. After cooling to room temperature, the mixture was acidified with 5 M sulfuric acid. The mixture was extracted with EtOAc. After washing with water, the organic layer was dried over magnesium sulfate, the solvent was removed under reduced pressure to give 5-(trifluoromethyl)cyclohexane-1,3-dione, which was used to the next step without further purification (98%). LC/MS (m/z): MH+=181.1, Rt=0.55 min.

Workup

  1. temperaturethe mixture refluxed for 1 h
  2. extractionThe mixture was extracted with EtOAc
  3. washAfter washing with water
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-be1de17ceecf4c13b9ad88d74901ce62
Source dataset
uspto-grants-2012_12
Patent number
US08329732B2

Reaction notes

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