Chloroacetone → 1-[6-(Acetyloxy)-2-benzofuranyl]ethanone

HRID 2369829Notes

Reaction equation

HRID 2369829 reaction equation
C([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=O)=[CH:5][C:4]=1O)=O.[C:14]([OH:17])(=[O:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:25][C:26](=[O:28])C>C(#N)C.C(OCC)(=O)C>[C:14]([O:17][C:3]1[CH:4]=[CH:5][C:6]2[CH:9]=[C:10]([C:26](=[O:28])[CH3:25])[O:12][C:7]=2[CH:8]=1)(=[O:16])[CH3:15]

Participants

6

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 86616952HCID 86616952, compound

Product 1

HCID 126480921-[6-(Acetyloxy)-2-benzofuranyl]ethanone

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a'solution of acetic acid 4-Formyl-3-hydroxyphenyl acetate (1.74 g, 9.67 mmol) in acetonitrile (10 mL) was added solid anhydrous potassium carbonate (1.33 g, 9.67 mmol) and stirred for 30 min at room temperature prior to the slow addition of chloroacetone (0.98 g, 9.67 mmol) via a syringe. A reflux condenser was attached and the reaction was heated to reflux overnight, then cooled to room temperature and diluted with ethyl acetate (350 mL). The organic layer was washed with 2.0 N aqueous HCl (100 mL), saturated aqueous sodium chloride (60 mL), dried over magnesium sulfate, filtered, and concentrated to afford crude product. Purification on silica (9:1 to 7:3, hexanes/ethyl, acetate) afforded the desired product together with the product without the acetate group. The total weight of the mixture obtained was 0.4421 g. This mixture was taken to the next step without further purification.

Workup

  1. customA reflux condenser was attached
  2. temperaturethe reaction was heated
  3. temperatureto reflux overnight
  4. temperaturecooled to room temperature
  5. washThe organic layer was washed with 2.0 N aqueous HCl (100 mL), saturated aqueous sodium chloride (60 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford crude product
  10. customPurification on silica (9:1 to 7:3, hexanes/ethyl, acetate)

Sources & evidence

ORD record
ord-bb15aa1e7c07495cbe3ce7bf5423a762
Source dataset
uspto-grants-2014_04
Patent number
US08710038B2

Reaction notes

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