Allyl bromide → HCID 10584282, compound

HRID 1722351Notes

Reaction equation

HRID 1722351 reaction equation
[CH:1]1([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[OH:12])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:13](Br)[CH:14]=[CH2:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:15]([O:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1)[CH:14]=[CH2:13]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 802852-Cyclopentylphenol

Product 1

HCID 10584282HCID 10584282, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

486.7 g (3.0 mol) of 2-cyclopentylphenol, 472 g (3.9 mol) of allyl bromide and 830 g (6.0 mol) of potassium carbonate are heated under reflux in 2.5 l of acetone while stirring vigorously for 26 h. The cooled reaction mixture is filtered, and the filtrate is concentrated in vacuo. The residue is taken up in petroleum ether, and the solution is washed three times with 2N sodium hydroxide solution. The organic phase is dried over magnesium sulfate and concentrated in vacuo, and the residue is finally distilled in vacuo. 593 g (97% of theory) of 2-cyclopentylphenyl allyl ether are obtained.

Workup

  1. customThe cooled reaction mixture
  2. filtrationis filtered
  3. concentrationthe filtrate is concentrated in vacuo
  4. washthe solution is washed three times with 2N sodium hydroxide solution
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. distillationthe residue is finally distilled in vacuo

Sources & evidence

ORD record
ord-8e094ef3640b4d4484b7d00c6e7e9640
Source dataset
uspto-grants-1989_08
Patent number
US04855323

Reaction notes

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