Isopropanol → HCID 58070832, compound

HRID 1193030Notes

Reaction equation

HRID 1193030 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[CH2:14]([O:21][C:22]1[CH:27]=[C:26]([CH3:28])[C:25]([CH:29]2[C:33](=[O:34])[CH:32]=[CH:31][CH:30]2[OH:35])=[C:24]([CH3:36])[CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CC(O)C>CC(C)=O.[Cl-].[Na+].O>[CH2:14]([O:21][C:22]1[CH:27]=[C:26]([CH3:28])[C:25]([CH:29]2[C:30](=[O:35])[CH:31]=[CH:32][C:33]2=[O:34])=[C:24]([CH3:36])[CH:23]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 58070862HCID 58070862, compoundHCID 131709961Jones' reagent

Product 1

HCID 58070832HCID 58070832, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of Jones reagent (1.67 M, 60 ml, 100 mmol) is added, dropwise, to a solution of 5-(4-benzyloxy-2,6-dimethylphenyl)-4-hydroxycyclopent-2-enone (30.9 g) in acetone (500 ml) at 0° C., and the resulting solution is stirred at 0° C. for 2 hours. Propan-2-ol (50 ml) is added and the mixture is stirred for a further 2 hours, then brine (200 ml) is added and the reaction mixture is extracted with ethyl acetate (2×250 ml). The organic extracts are combined, washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate is concentrated under reduced pressure. The residue is purified by column chromatography on silica gel to give 2-(4-benzyloxy-2,6-dimethylphenyl)cyclopent-4-ene-1,3-dione (18.1 g).

Workup

  1. extractionthe reaction mixture is extracted with ethyl acetate (2×250 ml)
  2. washwashed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-4e7939eba2704c759d9d9125f9e550b3
Source dataset
uspto-grants-2014_03
Patent number
US08680339B2

Reaction notes

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