Benzyl Bromide → HCID 3735677, compound

HRID 1737172Notes

Reaction equation

HRID 1737172 reaction equation
[Mg].[CH2:2](Br)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:10]1(=[O:16])[CH2:15][CH2:14][CH2:13][CH:12]=[CH:11]1>CCOCC.[Cu](I)I>[CH2:2]([C:12]1[CH2:13][CH2:14][CH2:15][C:10](=[O:16])[CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 7498Benzyl Bromide2×HCID 135942-Cyclohexen-1-oneHCID 5462224Magnesium

Product 1

HCID 3735677HCID 3735677, compoundYield 57.6%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
-20 °C

Procedure

A 500-ml four-necked flask equipped with a thermometer and a condenser was charged with 2.4 g of a piece of magnesium and 120 ml of absolute ether, to which a part of 17 g of benzyl bromide was added with heating. After a reaction started, the remaining amount of benzyl bromide was added dropwise to such a degree that reflux continued. After completion of the drop addition, the resultant mixture was stirred further for 1 hour at room temperature to obtain a liquid reaction mixture. A 500-ml four-necked flask equipped with a thermometer was charged with a suspension of 1 g of copper iodide in 60 ml of absolute ether, to which the liquid reaction mixture was added dropwise at -5° C. After stirring the resultant mixture for 1 hour at the same temperature, it was cooled to -20° C. A solution of 8.6 g of 2-cyclohexen-1-one in 10 ml of absolute ether was added dropwise to the mixture, and the temperature of the resulting liquid reaction mixture was then raised to room temperature while stirring for 24 hours. The liquid reaction mixture was washed with water, dried, filtered and concentrated, and 21 g of the resulting crude product were purified by column chromatography, thereby obtaining 9.6 g (yield: 57%) of 3-benzylcyclohexenone.

Workup

  1. customA 500-ml four-necked flask equipped with a thermometer and a condenser
  2. additionwas added
  3. temperaturewith heating
  4. temperaturethat reflux
  5. additionAfter completion of the drop addition
  6. customto obtain
  7. customa liquid reaction mixture
  8. customA 500-ml four-necked flask equipped with a thermometer
  9. customthe liquid reaction mixture
  10. additionwas added dropwise at -5° C
  11. customthe temperature of the resulting liquid reaction mixture
  12. temperaturewas then raised to room temperature
  13. customThe liquid reaction mixture
  14. washwas washed with water
  15. customdried
  16. filtrationfiltered
  17. concentrationconcentrated
  18. custom21 g of the resulting crude product were purified by column chromatography

Sources & evidence

ORD record
ord-c16d300c826f43c48cddf6dc17a4f33f
Source dataset
uspto-grants-1999_10
Patent number
US05962403

Reaction notes

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