Sulfuric Acid → 5-Benzyl-1-cyclooctanone

HRID 498107Notes

Reaction equation

HRID 498107 reaction equation
[CH2:1]([CH:8]1[CH2:15][CH2:14][CH2:13][CH:12]([OH:16])[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.S(=O)(=O)(O)O.[Cr](O)(O)(=O)=O>CC(C)=O.CC(O)C.O>[CH2:1]([CH:8]1[CH2:9][CH2:10][CH2:11][C:12](=[O:16])[CH2:13][CH2:14][CH2:15]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 24425Chromic AcidHCID 223197855-Benzyl-1-cyclooctanolHCID 131709961Jones' reagent

Product 1

HCID 223197995-Benzyl-1-cyclooctanoneYield 95.5%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

1.3 g of 5-benzyl-1-cyclooctanol prepared in the aforementioned Reference Example 1 was dissolved in 40 ml of acetone. To the solution was added 2.5 ml Jones reagent which was prepared in the ratio of 11.5 ml of sulfuric acid, 13 g of chromic acid and 20 ml of water. The reaction solution was stirred at room temperature for twenty minutes. To the reaction solution was added 2 ml of 2-propanol, followed by filtration through Celite. The residue was washed with dichloromethane and the washing liquid was combined with the filtrate. The filtrate was washed with water and a saturated saline solution, and dried over anhydrous sodium sulfate. The solvent was evaporated. The crude product was subject to column chromatography on silica gel, and the eluate with ethyl acetate-hexane (1:15) was collected, to afford 1.23 g of the titled compound as colorless liquid.

Workup

  1. filtrationfollowed by filtration through Celite
  2. washThe residue was washed with dichloromethane
  3. washThe filtrate was washed with water
  4. dry with materiala saturated saline solution, and dried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customthe eluate with ethyl acetate-hexane (1:15) was collected

Sources & evidence

ORD record
ord-50ab3ba66e804738bd9578007c15a711
Source dataset
uspto-grants-2005_09
Patent number
US06949585B2

Reaction notes

Loading…