Propargyl bromide → Propargyl ether

HRID 743416

Reaction equation

HRID 743416 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)([C:11]([F:14])([F:13])[F:12])[C:4]1[CH:10]=[CH:9][C:7]([OH:8])=[CH:6][CH:5]=1.[CH2:24](Br)[C:25]#[CH:26].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:26]([O:21][CH2:18][C:19]#[CH:20])[C:25]#[CH:24].[F:1][C:2]([F:22])([F:23])[C:3]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)([C:11]([F:13])([F:14])[F:12])[C:4]1[CH:10]=[CH:9][C:7]([OH:8])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 73864bisphenol AF

Product 2

HCID 23349Propargyl etherHCID 73864bisphenol AF

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 168.12 g. (0.5 mole) of hexafluorobisphenol A in 1000 ml of acetone was reacted with 142.76 g. (1.2 moles) of propargyl bromide in the presence of 165.85 g. (1.2 moles) of potassium carbonate. The reaction mixture was stirred and heated under reflux for 72 hrs. After cooling it was filtered and the solvent (acetone) of the filtrate was evaporated on a Buchi Re 121 Rotavapor. The residue was dissolved in diethyl ether and washed first with a 5% NaOH solution and then three times with deionized water. Dipropargyl ether of hexafluorobisphenol A was obtained in 90% yield after evaporation of diethyl ether on a Rotavapor. The product was a light brown liquid with the following structure. ##STR11##

Workup

  1. temperatureheated
  2. temperatureunder reflux for 72 hrs
  3. temperatureAfter cooling it
  4. filtrationwas filtered
  5. customthe solvent (acetone) of the filtrate was evaporated on a Buchi Re 121 Rotavapor
  6. dissolutionThe residue was dissolved in diethyl ether
  7. washwashed first with a 5% NaOH solution

Sources & evidence

ORD record
ord-57033bdd4c22439aaf34b4eca7fcf324
Source dataset
uspto-grants-1996_09
Patent number
US05556921

Linked notes

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