Methyl iodide → p-tert-Butylanisole

HRID 1389557Notes

Reaction equation

HRID 1389557 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CI.[C:14](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:11][CH3:14])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 73934-tert-ButylphenolHCID 11430Potassium Carbonate

Product 1

HCID 94750p-tert-ButylanisoleYield 94.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 15.0 g of 4-tert-butylphenol dissolved in 100 ml of acetone were added 37.5 ml of methyl iodide and 83.0 g of potassium carbonate and heated at reflux for 20 hours. The reaction mixture was filtered and the filtrate was concentrated at reduced pressure. Diethyl ether was added to the residue to remove the insoluble matters by the filtration and the filtrate was concentrated at reduced pressure. The residue was purified by vacuum distillation to give 15.5 g of the title compound having the following physical properties.

Workup

  1. temperatureheated
  2. temperatureat reflux for 20 hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated at reduced pressure
  5. additionDiethyl ether was added to the residue
  6. customto remove the insoluble matters
  7. filtrationby the filtration
  8. concentrationthe filtrate was concentrated at reduced pressure
  9. distillationThe residue was purified by vacuum distillation

Sources & evidence

ORD record
ord-2d1ad869ed404d58ba0aae6f90ccf112
Source dataset
uspto-grants-1981_01
Patent number
US04245099

Reaction notes

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