Potassium Iodide → (4-benzyloxy-3,5-dimethoxy-phenyl)-acetic Acid Methyl Ester

HRID 1723997Notes

Reaction equation

HRID 1723997 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([OH:13])=[C:7]([O:14][CH3:15])[CH:6]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O.O>[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[CH:6]=[C:7]([O:14][CH3:15])[C:8]([O:13][CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[C:9]([O:11][CH3:12])[CH:10]=1

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 57436869Methyl 2-(4-hydroxy-3,5-dimethoxyphenyl)acetate

Product 1

HCID 57436870(4-benzyloxy-3,5-dimethoxy-phenyl)-acetic Acid Methyl EsterYield 52.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of (4-hydroxy-3,5-dimethoxy-phenyl)-acetic acid methyl ester (4.1 g, 18.1 mmol) in acetone (50 mL) was added potassium carbonate (1.39 g, 10.1 mmol) benzyl chloride (3.58 g, 28.28 mmol) and potassium iodide (catalytic amount). After completion of addition the reaction mixture was heated to reflux overnight. The next day, the reaction was cooled down to room temperature and diluted with water. The aqueous layer was extracted with ethyl acetate. All combined organic layers were dried over sodium sulfate, filtered, and concentrated. The crude material was purified using silica gel chromatography (gradient 100% pentane to 100% ethyl acetate) to afford the desired compound (1.5 g, 26%).

Workup

  1. additionAfter completion of addition the reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux overnight
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialwere dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified

Sources & evidence

ORD record
ord-94b24e2f93254c65bf546b19f892e2bb
Source dataset
uspto-grants-2009_02
Patent number
US07485283B2

Reaction notes

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