Acetic Anhydride → HCID 66842179, compound

HRID 226093Notes

Reaction equation

HRID 226093 reaction equation
[C:1]([C:4]1[C:14]([OH:15])=[CH:13][CH:12]=[CH:11][C:5]=1[O:6][CH2:7]C(O)=O)(=O)[CH3:2].[C:16](OC(=O)C)(=O)C.C([O-])(=O)C.[Na+]>O>[CH3:7][O:6][C:5]1[C:4]2[C:1]([CH3:2])=[CH:16][O:15][C:14]=2[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 12391063HCID 12391063, compound

Product 1

HCID 66842179HCID 66842179, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

(2-Acetyl-3-hydroxy-phenoxy)-acetic acid (2.0 g, 8.9 mmol) is added to acetic anhydride (60 ml) followed by sodium acetate (10.0 g, 122.0 mmol). The mixture is stirred and heated to 110° C., under a nitrogen atmosphere, for 5 hrs. then cooled to 0° C. Water (100 ml) is added slowly, stirred while warming to ambient temperature and continued stirring overnight. The solution is extracted twice with ethyl acetate and the combined organic extracts are washed twice with sodium hydroxide (1N), then brine, dried over Na2SO4, filtered and concentrated. The crude product is purified by chromatography using a hexane-ethyl acetate gradient (100% hexane to 25% ethyl acetate in hexane) to give the title compound (1.2 g, 83% yield).

Workup

  1. temperaturethen cooled to 0° C
  2. stirringstirred
  3. temperaturewhile warming to ambient temperature
  4. stirringcontinued stirring overnight
  5. extractionThe solution is extracted twice with ethyl acetate
  6. washthe combined organic extracts are washed twice with sodium hydroxide (1N)
  7. dry with materialbrine, dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product is purified by chromatography

Sources & evidence

ORD record
ord-979aef50ec9b4c8dbfcf55e678013173
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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