Phenol → Phenyl glycidyl ether

HRID 544417Notes

Reaction equation

HRID 544417 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:14]([CH:16]1[O:18][CH2:17]1)Cl>CC(C)=O.C1(C)C=CC=CC=1>[O:18]1[CH2:17][CH:16]1[CH2:14][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 7835EpichlorohydrinHCID 11430Potassium Carbonate

Product 1

HCID 31217Phenyl glycidyl etherYield 60%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1140TolueneSolvent

Procedure

A mixture of 9.4 gm (0.1 mole) of phenol, 28 gm (0.2 mole) of potassium carbonate and 30 mL (0.4 mole) of epichlorohydrin in 250 mL acetone was heated to reflux for 12 hours. The reaction medium was then filtered and evaporated leaving an oil which was taken up in toluene and successively washed with 100 mL water, 2×100 mL 1.0 N sodium hydroxide and 2×100 mL water. The toluene phase was dried with magnesium sulfate and evaporated to provide a clear oil which was chromatographed on a Prep-500 silica gel column employing hexane: ethyl acetate (9:1) as the mobile phase. Collection of the major peak and evaporation of solvent provided 9 gm (60%) of a clear oil whose NMR and IR spectra were consistent with the assigned structure.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 12 hours
  3. filtrationThe reaction medium was then filtered
  4. customevaporated
  5. customleaving an oil which
  6. washsuccessively washed with 100 mL water, 2×100 mL 1.0 N sodium hydroxide and 2×100 mL water
  7. dry with materialThe toluene phase was dried with magnesium sulfate
  8. customevaporated
  9. customto provide a clear oil which
  10. customwas chromatographed on a Prep-500 silica gel column
  11. customCollection of the major peak and evaporation of solvent

Sources & evidence

ORD record
ord-b1b9a6b193e34b5d8e0fb30e3ab390fe
Source dataset
uspto-grants-1984_05
Patent number
US04450173

Reaction notes

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