Isopropanol → 4-(2-Hydroxy-1,1,1-trifluoro-2-propyl)cyclohexanone

HRID 1419793Notes

Reaction equation

HRID 1419793 reaction equation
[OH:1][C:2]([CH:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)([CH3:7])[C:3]([F:6])([F:5])[F:4].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C.C(=O)(O)[O-].[Na+]>CC(C)=O.O>[OH:1][C:2]([CH:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)([CH3:7])[C:3]([F:5])([F:6])[F:4]

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 516892Sodium BicarbonateHCID 539089674-(2-Hydroxy-1,1,1-trifluoro-2-propyl)cyclohexanolHCID 131709961Jones' reagent

Product 1

HCID 144129814-(2-Hydroxy-1,1,1-trifluoro-2-propyl)cyclohexanone

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

18.8 g (0.089 mol) of 4-(2-hydroxy-1,1,1-trifluoro-2-propyl)cyclohexanol were placed in a mixture of 350 ml of acetone and 20 ml of water, and 50 ml of Jones' reagent were added dropwise at from 10° to 15° C. The mixture was subsequently stirred at room temperature for 1 hour, 10 ml of isopropanol were added, and after a further 30 minutes the mixture was neutralized with 40 g of sodium bicarbonate. It was then filtered, the filtrate was concentrated and the residue was taken up with water/diethyl ether. After drying and concentration of the organic phase, 11.1 g (59.6% of theory) remained of a colorless product.

Workup

  1. additionwere added dropwise at from 10° to 15° C
  2. filtrationIt was then filtered
  3. concentrationthe filtrate was concentrated
  4. customAfter drying

Sources & evidence

ORD record
ord-24af8181729d4a4489a6fb8ab09eeeed
Source dataset
uspto-grants-1999_03
Patent number
US05889012

Reaction notes

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