Phenol → Allyl phenyl ether

HRID 1771115Notes

Reaction equation

HRID 1771115 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:15][CH:16]=[CH2:17]>CC(C)=O>[CH2:17]([O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH:16]=[CH2:15]

Participants

5

Reactant 3

HCID 996PhenolHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 74458Allyl phenyl etherYield 90.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

94 g phenol (1 mol), 155 g anhydrous potassium carbonate (1.2 mol) and 300 mL acetone were added to a three-necked bottle, and stirred at 50° C. for 10 minutes. 107 g 3-bromopropylene (0.9 mol) was added dropwise, then the mixture was refluxed for 2 hours. After acetone was evaporated under reduced pressure, water was added to the residual solution and a solid was isolated. After sucked filtration, 108 g solid was obtained. Yield: 90.1%. MS: 135 (M+1).

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. customAfter acetone was evaporated under reduced pressure, water
  3. additionwas added to the residual solution
  4. customa solid was isolated
  5. filtrationfiltration

Sources & evidence

ORD record
ord-21a5ab0a875349259c942e9c82150ae7
Source dataset
uspto-grants-2016_02
Patent number
US09249106B2

Reaction notes

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