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

HRID 1417827Notes

Reaction equation

HRID 1417827 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-b7264f0e523c441786a0f8e06acdd1a6
Source dataset
uspto-grants-1999_03
Patent number
US05877317

Reaction notes

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