Water → 5-Benzyl-2-cycloocten-1-one

HRID 498108Notes

Reaction equation

HRID 498108 reaction equation
[CH2:1]([CH:8]1[CH2:15][CH2:14][CH2:13][C:12](=[O:16])[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1([Se]Cl)C=CC=CC=1.O>C(OCC)(=O)C>[CH2:1]([CH:8]1[CH2:15][CH2:14][CH2:13][C:12](=[O:16])[CH:11]=[CH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21928ChloroselenobenzeneHCID 223197995-Benzyl-1-cyclooctanone

Product 1

HCID 697660575-Benzyl-2-cycloocten-1-oneYield 59.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.2 g of 5-benzyl-1-cyclooctanone prepared in Example 1 was dissolved in 50 ml of ethyl acetate. To the solution was added 1.25 g of phenylselenenylchloride. The reaction solution was stirred at room temperature for forty minutes. To the reaction solution was added 10 ml of water, followed by stirring for three minutes. The organic layer was separated. To the organic layer were added 20 ml of tetrahydrofliran and 1.4 ml of 30% hydrogen peroxide. The reaction solution was stirred at room temperature for two and a half hours. Then, the organic layer was washed with water and a saturated sodium bicarbonate aqueous 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 (1:10) was collected, to afford 0.71 g of the titled compound as colorless liquid.

Workup

  1. stirringby stirring for three minutes
  2. customThe organic layer was separated
  3. additionTo the organic layer were added 20 ml of tetrahydrofliran and 1.4 ml of 30% hydrogen peroxide
  4. stirringThe reaction solution was stirred at room temperature for two and a half hours
  5. washThen, the organic layer was washed with water
  6. dry with materiala saturated sodium bicarbonate aqueous solution, and dried over anhydrous sodium sulfate
  7. customThe solvent was evaporated
  8. customthe eluate with ethyl acetate-hexane (1:10) was collected

Sources & evidence

ORD record
ord-c8646102da9f49938acf285671d75ecd
Source dataset
uspto-grants-2005_09
Patent number
US06949585B2

Reaction notes

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