Acetic Acid → HCID 86681917, compound

HRID 1749721Notes

Reaction equation

HRID 1749721 reaction equation
C([CH2:4][O:5][C:6]1[C:14]([CH3:15])=[CH:13][C:12]([O:16][CH3:17])=[CH:11][C:7]=1[C:8]([OH:10])=O)(O)=O.C(O)(=O)C.C(OC(=O)C)(=O)C.C([O-])(=O)C.[Na+]>CCCCCC.C(OCC)(=O)C.C(OCC)(=O)C>[CH3:17][O:16][C:12]1[CH:13]=[C:14]([CH3:15])[C:6]2[O:5][CH2:4][C:8](=[O:10])[C:7]=2[CH:11]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 71278795HCID 71278795, compound

Product 1

HCID 86681917HCID 86681917, compoundYield 8.8%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
120 °C

Procedure

The synthesis was performed with reference to the known literature (Bioorganic & Medicinal Chemistry Letters, Vol. 17, p. 6354, 2007). 2-(Carboxymethoxy)-5-methoxy-3-methylbenzoic acid (3.9 g, 16 mmol) was successively added with acetic acid (12 mL), acetic anhydride (20 mL), and sodium acetate (4.0 g), and the mixture was stirred at 120° C. for 4 hours. The reaction mixture was added with ethyl acetate, and the organic layer was successively washed with water, saturated aqueous sodium hydrogencarbonate, and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, the residue was successively added with methanol (40 mL), water (10 mL), and concentrated hydrochloric acid (1.0 mL), and the mixture was refluxed for 1 hour by heating. The solvent was evaporated under reduced pressure, then the residue was dissolved in ethyl acetate, and the solution was washed successively with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the solid formed was suspended in hexane/ethyl acetate (90:10) and thereby washed to obtain 5-methoxy-7-methylbenzofuran-3(2H)-one (0.25 g, 8%).

Workup

  1. washthe organic layer was successively washed with water, saturated aqueous sodium hydrogencarbonate, and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. additionthe residue was successively added with methanol (40 mL), water (10 mL), and concentrated hydrochloric acid (1.0 mL)
  5. temperaturethe mixture was refluxed for 1 hour
  6. temperatureby heating
  7. customThe solvent was evaporated under reduced pressure
  8. dissolutionthe residue was dissolved in ethyl acetate
  9. washthe solution was washed successively with water and saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was evaporated under reduced pressure
  12. customthe solid formed
  13. washwashed

Sources & evidence

ORD record
ord-d46df9e0f3db4ed0903b6d36afc4be27
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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