Isopropanol → HCID 22400486, compound

HRID 260826Notes

Reaction equation

HRID 260826 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([O:16][CH2:17][CH2:18][CH2:19][OH:20])[CH2:12][CH2:13][CH2:14][CH3:15])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].CC(C)=[O:23].OS(O)(=O)=O.O=[Cr](=O)=O.CC(O)C.C(OCC)(=O)C>CC(C)=O>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([O:16][CH2:17][CH2:18][C:19]([OH:23])=[O:20])[CH2:12][CH2:13][CH2:14][CH3:15])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 8857Ethyl AcetateHCID 22400464HCID 22400464, compoundHCID 131709961Jones' reagent

Product 1

HCID 22400486HCID 22400486, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Chromium(VI) oxide was dissolved in an aqueous solution of sulfuric acid, and diluted with water to give a Jones reagent. To a solution of 3-[1-(4-isobutylphenyl)pentyloxy]propanol in acetone was added the obtained Jones reagent at room temperature until an orange-brown color persisted. After 10 minutes, 2-propanol was added to the reaction mixture. Ethyl acetate was added thereto, and the mixture was washed with water and brine, dried over magnesium sulfate and concentrated. Silica gel column chromatography of the concentrate afforded the object compound.

Workup

  1. washthe mixture was washed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customSilica gel column chromatography of the concentrate afforded the object compound

Sources & evidence

ORD record
ord-3ab50bd9122f4217889e0ddcac307b39
Source dataset
uspto-grants-1996_06
Patent number
US05530019

Reaction notes

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