Water → HCID 21101203, compound

HRID 1352846Notes

Reaction equation

HRID 1352846 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:15][O:16][CH2:17]Cl.O>CC(C)=O>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:15][O:16][CH3:17])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl Ether2×HCID 11430Potassium Carbonate2×HCID 122723-Iodophenol

Product 1

HCID 21101203HCID 21101203, compoundYield 102.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of m-iodophenol (3.00 g, 13.6 mmol) in acetone (30 ml) were added potassium carbonate (2.30 g, 16.6 mmol) and chloromethyl methyl ether (1.20 g, 14.9 mmol) under ice cooling and the mixture was stirred for 65 hours at room temperature. To the reaction mixture were further added potassium carbonate (0.600 g, 4.30 mmol) and chloromethyl methyl ether (0.300 g, 3.70 mmol), and the mixture was stirred for 2 hours at room temperature. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium chloride solution, and dried over magnesium sulfate. The solvent was removed under reduced pressure to give the subject compound (3.68 g, 102%).

Workup

  1. stirringthe mixture was stirred for 2 hours at room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with an aqueous saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8cf622324e304024bb78190709e358be
Source dataset
uspto-grants-2007_05
Patent number
US07220773B2

Reaction notes

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