2,5-Dichlorophenol → 2,5-Dichloroanisole

HRID 1735645Notes

Reaction equation

HRID 1735645 reaction equation
[C:1]([O-:4])([O-])=O.[K+].[K+].CI.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1O>CC(C)=O>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[O:4][CH3:1]

Participants

5

Reactant 3

HCID 662,5-DichlorophenolHCID 6328Methyl iodideHCID 11430Potassium Carbonate

Product 1

HCID 161252,5-DichloroanisoleYield 93.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Anhydrous K2CO3 (21.9 g, 0.159 mol) and methyl iodide (10.8 mL, 0.178 mol) were added to a solution of 2,5-dichlorophenol (23.5 g, 0.144 mol) in 215 mL acetone. The reaction was allowed to stir at room temperature for 20 hours, then filtered through a celite pad. The filtrate was concentrated to a residue which was taken up in diethylether. The ether solution was washed with 10% NaHSO3, water, several portions of 1M NaOH, and brine, then dried with anhydrous Na2SO4. Upon filtration and concentration, the residue was distilled (8 mm Hg, 110° C.) to yield 23.7 g (93.5%) of a light yellow oil.

Workup

  1. filtrationfiltered through a celite pad
  2. concentrationThe filtrate was concentrated to a residue which
  3. washThe ether solution was washed with 10% NaHSO3, water, several portions of 1M NaOH, and brine
  4. dry with materialdried with anhydrous Na2SO4
  5. filtrationUpon filtration and concentration
  6. distillationthe residue was distilled (8 mm Hg, 110° C.)

Sources & evidence

ORD record
ord-0ceed072c755442e9e24d1171afeeae2
Source dataset
uspto-grants-1996_07
Patent number
US05538852

Reaction notes

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