4-tert-Butylphenol → p-tert-Butylphenyl glycidyl ether

HRID 1596468Notes

Reaction equation

HRID 1596468 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)Cl.[C:6]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)([CH3:9])([CH3:8])[CH3:7].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:6]([C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:1][CH:3]2[CH2:4][O:5]2)=[CH:14][CH:15]=1)([CH3:9])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 73934-tert-ButylphenolHCID 7835EpichlorohydrinHCID 11430Potassium Carbonate

Product 1

HCID 18360p-tert-Butylphenyl glycidyl etherYield 76.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of epichlorohydrin (15.3 g; 0.165 mol), 4-tert-butylphenol (5.0 g; 0.033 mol) and potassium carbonate (6.9 g; 0.050 mol) in acetonitrile (50 mL) was refluxed for 5 h. The resulting heterogeneous mixture was cooled to below reflux temperature and vacuum filtered through fritted glass. The organics were concentrated to give the crude product (7.9 g) as a liquid. Flash chromatography on silica gel (CH2Cl2:EtOAc; 19:1) gave the desired product (5.2 g; 76%) as a liquid.

Workup

  1. temperaturewas refluxed for 5 h
  2. temperatureThe resulting heterogeneous mixture was cooled
  3. temperatureto below reflux temperature and vacuum
  4. filtrationfiltered through fritted glass
  5. concentrationThe organics were concentrated
  6. customto give the crude product (7.9 g) as a liquid

Sources & evidence

ORD record
ord-39d5e7b2d30a462a93536e6f1e65f847
Source dataset
uspto-grants-2001_09
Patent number
US06291475B1

Reaction notes

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