Methyl iodide → 4-METHOXYISOBENZOFURAN-1(3H)-ONE

HRID 1091801Notes

Reaction equation

HRID 1091801 reaction equation
IC.[OH:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][O:7][C:8]2=[O:13].[C:14](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:14][O:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][O:7][C:8]2=[O:13]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 126620774-Hydroxyisobenzofuran-1(3H)-one

Product 1

HCID 111163794-METHOXYISOBENZOFURAN-1(3H)-ONEYield 93.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Iodomethane (1.313 mL, 20.78 mmol) was added to 4-hydroxyisobenzofuran-1(3H)-one (3.12 g, 20.78 mmol) and potassium carbonate (5.74 g, 41.56 mmol) in DMF (50 mL) at 21° C. under air. The resulting solution was stirred overnight. The solvent was removed to give a yellow solid which was then quenched with potassium carbonate (70 ml). The mixture was extracted ethyl acetate (3×75 ml). The combined extracts were evaporated to give the desired material as a yellow solid (3.18 g, 93% yield), which was used without further purification; 1H NMR (400.132 MHz, CDCl3) δ 3.30 (2H, s), 5.37 (2H, s), 7.31-7.42 (2H, m), 7.51-7.61 (1H, m).

Workup

  1. customThe solvent was removed
  2. customto give a yellow solid which
  3. customwas then quenched with potassium carbonate (70 ml)
  4. extractionThe mixture was extracted ethyl acetate (3×75 ml)
  5. customThe combined extracts were evaporated

Sources & evidence

ORD record
ord-9a2fbbc23a6c42949c4723360b04603b
Source dataset
uspto-grants-2012_03
Patent number
US08129380B2

Reaction notes

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