Methanol → Methyl (3-oxo-1,3-dihydro-2-benzofuran-1-yl)acetate

HRID 368846Notes

Reaction equation

HRID 368846 reaction equation
[C:1]1([C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([CH2:11][C:12]([OH:14])=[O:13])[O:3]1)=[O:2].[CH3:15]O>Cl>[C:1]1([C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[O:3]1)=[O:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 5897301,3-Dihydro-3-oxo-1-isobenzofuranacetic acid

Product 1

HCID 3095117Methyl (3-oxo-1,3-dihydro-2-benzofuran-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Phthalide-3-acetic acid (XCI, 9.6 g, 50 mmol) is dissolved in methanol (50 ml) saturated with anhydrous hydrochloric acid and the mixture is cooled to 0-5° for 18 hr. The solvent is concentrated under reduced pressure, treated with sodium bicarbonate, and extracted with methylene chloride (800 ml). The organic phase is washed with saturated aqueous sodium bicarbonate, saline, dried over magnesium sulfate, filtered and concentrated to give the title compound, mp 62-63°; NMR (CDCl3, TMS) 7.94-7.50, 5.90, 3.77 and 2.92 δ.

Workup

  1. temperaturethe mixture is cooled to 0-5° for 18 hr
  2. concentrationThe solvent is concentrated under reduced pressure
  3. additiontreated with sodium bicarbonate
  4. extractionextracted with methylene chloride (800 ml)
  5. washThe organic phase is washed with saturated aqueous sodium bicarbonate, saline
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9a9804a6a5c34941a5893d98cb66ee05
Source dataset
uspto-grants-2000_10
Patent number
US06133446

Reaction notes

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