Isopropanol → 2-(2,4,6-Trimethylphenyl)cyclopent-4-ene-1,3-dione

HRID 407844Notes

Reaction equation

HRID 407844 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[CH3:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:16]=1[CH:23]1[C:27](=[O:28])[CH:26]=[CH:25][CH:24]1[OH:29].C(O)(C)C>CC(C)=O.C(OCC)(=O)C>[CH3:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:16]=1[CH:23]1[C:24](=[O:29])[CH:25]=[CH:26][C:27]1=[O:28]

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 666840085-(2,4,6-Trimethylphenyl)-4-hydroxycyclopent-2-enoneHCID 131709961Jones' reagent

Product 1

HCID 666844242-(2,4,6-Trimethylphenyl)cyclopent-4-ene-1,3-dione

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Jones' reagent (138 ml of 1.67 M solution, 230 mmol) is added dropwise over 40 minutes to a cooled (ice-bath) solution of 5-(2,4,6-trimethylphenyl)-4-hydroxycyclopent-2-enone (49.66 g, 230 mmol) in acetone (600 ml). The mixture is stirred for 1 hour. Isopropanol (100 ml) is added and the mixture is stirred at room temperature for 2 hours. The mixture is diluted with ethyl acetate and washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure to give 2-(2,4,6-trimethylphenyl)cyclopent-4-ene-1,3-dione.

Workup

  1. stirringthe mixture is stirred at room temperature for 2 hours
  2. washwashed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-a347cd50830b441ba7f4871313aa4c12
Source dataset
uspto-grants-2014_06
Patent number
US08754242B2

Reaction notes

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