4-Chlorophenol → 4-Chloroanisole

HRID 968329Notes

Reaction equation

HRID 968329 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.CI.[C:11](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 6328Methyl iodideHCID 11430Potassium Carbonate

Product 1

HCID 121674-ChloroanisoleYield 75%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

p-Chlorophenol (2 g, 15 mmol), methyl iodide (1.36 ml, 21.8 mmol) and potassium carbonate (2.07 g, 15.6 mmol) in dry acetone (15 ml) were taken in a 50 ml flask. After refluxing for 3 hrs at 60° C., acetone was removed using a rotary evaporator. Water was added and the product was extracted with CH2Cl2 to afford 2.2 g of crude product, which was purified by column chromatography using hexane as eluent to yield p-chloroanisole in 75% yield (1.59 g).

Workup

  1. customacetone was removed
  2. customa rotary evaporator
  3. additionWater was added
  4. extractionthe product was extracted with CH2Cl2
  5. customto afford 2.2 g of crude product, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-ecabf6d57f114c1d86a630493609bf0e
Source dataset
uspto-grants-2005_10
Patent number
US06958352B2

Reaction notes

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