Water → 1-(2-Bromoethoxy)-4-(2-propenyloxy)benzene

HRID 894971Notes

Reaction equation

HRID 894971 reaction equation
[Br:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[CH2:12](Br)[CH:13]=[CH2:14].C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O.CCCCCC>[Br:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:14][CH:13]=[CH2:12])=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 128339324-(2-Bromoethoxy)phenol

Product 1

HCID 129411171-(2-Bromoethoxy)-4-(2-propenyloxy)benzene

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8058HexaneSolvent

Procedure

To a solution of 45.0 g of 4-(2-bromoethoxy)-phenol (0.207 mol) in 310 ml of acetone was added 54 ml of allyl bromide (0.619 mol) and 45.0 g of anhydrous potassium carbonate (0.326 mol). The reaction mixture was stirred under reflux for eleven hours and was cooled and poured into 2500 ml of water. The mixture was extracted twice with 3:1 ether:methylene-chloride, and the organic layers were washed twice with 1 N NaOH, once with H2O, dried (Na2SO4) and concentrated to dryness under reduced pressure to yield a colorless oil. The analytical sample was prepared by crystallization from hexane to give colorless crystals, mp 27°-28°.

Workup

  1. temperatureunder reflux for eleven hours
  2. temperaturewas cooled
  3. extractionThe mixture was extracted twice with 3:1 ether
  4. washmethylene-chloride, and the organic layers were washed twice with 1 N NaOH, once with H2O
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated to dryness under reduced pressure
  7. customto yield a colorless oil
  8. customto give colorless crystals, mp 27°-28°

Sources & evidence

ORD record
ord-b79aea8a5773451d87c868bc827ae28d
Source dataset
uspto-grants-1981_08
Patent number
US04285873

Reaction notes

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