Sodium Acetate → Acetic acid 3-oxo-2,3-dihydro-benzofuran-6-ylmethyl ester

HRID 222460Notes

Reaction equation

HRID 222460 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:15]=[CH:14][C:8]([CH2:9][O:10][C:11](=[O:13])[CH3:12])=[CH:7][C:6]=1[OH:16])=[O:4].C([O-])(=O)C.[Na+]>CO>[O:4]=[C:3]1[C:5]2[CH:15]=[CH:14][C:8]([CH2:9][O:10][C:11](=[O:13])[CH3:12])=[CH:7][C:6]=2[O:16][CH2:2]1

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 86637759Acetic acid 4-(2-chloro-acetyl)-3-hydroxy-benzyl ester

Product 1

HCID 68526065Acetic acid 3-oxo-2,3-dihydro-benzofuran-6-ylmethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of acetic acid 4-(2-chloro-acetyl)-3-hydroxy-benzyl ester (2.20 g, 9.07 mmol) and sodium acetate (1.49 g, 18.13 mmol) in anhydrous methanol (40 mL) was heated to reflux for 2 h. The reaction mixture was allowed to cool to RT, and concentrated. The residue was dissolved in dichloromethane and washed with water. The aqueous phase was extracted with dichloromethane. The combined organic layers were dried over Na2SO4, evaporated in vacuo, and the residue was purified by column chromatography (ethylacetate:hexane; 2:8) to give the acetic acid 3-oxo-2,3-dihydro-benzofuran-6-ylmethyl ester as an off white solid (1.29 g, 59%). 1H NMR (CDCl3, 400 MHz) 2.17 (s, 3H), 4.65 (s, 2H), 5.17 (s, 2H), 7.06 (d, J=8.0 Hz, 1H), 7.13 (s, 1H), 7.67 (d, J=8.0 Hz, 1H), 11.67 (s, 1H), 13C NMR (CDCl3, 100 MHz) 20.8, 65.3, 75.1, 112.3, 120.8, 121.2, 124.2, 146.9, 170.5, 174.2, 199.2.

Workup

  1. temperatureto reflux for 2 h
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with water
  5. extractionThe aqueous phase was extracted with dichloromethane
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. customevaporated in vacuo
  8. customthe residue was purified by column chromatography (ethylacetate:hexane; 2:8)

Sources & evidence

ORD record
ord-2e863467ecc04178a1b36d8d8f94c04a
Source dataset
uspto-grants-2012_06
Patent number
US08207216B2

Reaction notes

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