Acetone → 2,4-Bis(allyloxy)-1-ethylbenzene

HRID 495306Notes

Reaction equation

HRID 495306 reaction equation
[CH2:1]([C:3]1[CH:9]=[CH:8][C:6]([OH:7])=[CH:5][C:4]=1[OH:10])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[CH:18]=[CH2:19].[CH3:21][C:22]([CH3:24])=O>>[CH2:17]([O:10][C:4]1[CH:5]=[C:6]([O:7][CH2:24][CH:22]=[CH2:21])[CH:8]=[CH:9][C:3]=1[CH2:1][CH3:2])[CH:18]=[CH2:19]

Participants

5

Reactant 4

HCID 180AcetoneHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 179274-Ethylresorcinol

Product 1

HCID 45498682,4-Bis(allyloxy)-1-ethylbenzeneYield 95%

Procedure

4-Ethylresorcinol (10 g, 73 mmol) was dissolved in acetone (250 mL), and potassium carbonate (30 g, 220 mmol) and allyl bromide (15 mL, 170 mmol) were added thereto and heated under reflux for 4 hours. The reaction mixture was cooled to room temperature, then filtered through Celite, and the filtrate was concentrated under reduced pressure. The resulting residue was purified through silica gel column chromatography (ethyl acetate/n-hexane=1/9) to obtain 2,4-bis(allyloxy)-1-ethylbenzene (15 g, 95%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. filtrationfiltered through Celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified through silica gel column chromatography (ethyl acetate/n-hexane=1/9)

Sources & evidence

ORD record
ord-a972cf91d66a4022bfea1f8451cc6534
Source dataset
uspto-grants-2009_05
Patent number
US07538241B2

Reaction notes

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