Methyl iodide → Methyl 2-(3-formylphenoxy)acetate

HRID 2117600Notes

Reaction equation

HRID 2117600 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[O:6][CH2:7][C:8]([OH:10])=[O:9])=[O:2].[C:14](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C.O>[CH3:14][O:9][C:8](=[O:10])[CH2:7][O:6][C:5]1[CH:11]=[CH:12][CH:13]=[C:3]([CH:1]=[O:2])[CH:4]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 6018952-(3-Formylphenoxy)acetic acid

Product 1

HCID 1494380Methyl 2-(3-formylphenoxy)acetateYield 87.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of (3-formyl-phenoxy)-acetic acid (3.6 g, 20.0 mmol), potassium carbonate (3.30 g, 23.9 mmol) and methyl iodide (1.86 g, 30.0 mmol) in 25 mL DMF was heated to 110° C. for 2 hours and was stirred at room temperature for 16 h. The mixture was diluted with water and the aqueous solution was extracted with EtOAc. The organic solution was washed with water, dried over MgSO4, filtered and concentrated in vacuo. The product was purified via silica gel chromatography (4:1 hexanes: EtOAc) to afford the title compound as a pale yellow oil (3.4 g). 1H NMR (400 MHz, CDCl3) δ 9.94 (s, 1H), 7.48 (m, 2H), 7.33 (s, 1H), 7.23 (m, 1H), 4.68 (s, 2H), 3.79 (s, 3H).

Workup

  1. extractionthe aqueous solution was extracted with EtOAc
  2. washThe organic solution was washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe product was purified via silica gel chromatography (4:1 hexanes: EtOAc)

Sources & evidence

ORD record
ord-3ac327c09a754f7e9db19f66995e6d41
Source dataset
uspto-grants-2008_10
Patent number
US07442702B2

Reaction notes

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