Ethyl Acetate → HCID 58566366, compound

HRID 1876393Notes

Reaction equation

HRID 1876393 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:13]([OH:15])=[O:14])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]=2[CH:12]=1.S(OOS([O-])(=O)=O)([O-])(=O)=[O:17].[K+].[K+].C(#N)C.O.C(OCC)(=O)C>O>[Cl:1][C:2]1[CH:3]=[C:4]([C:13]([OH:15])=[O:14])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[C:7](=[O:17])[C:6]=2[CH:12]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24412Potassium PersulfateHCID 101769185-Chloro-2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylic acidHCID 18373917Acetonitrile--water (1/1)

Product 1

HCID 58566366HCID 58566366, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5-chloro-2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylic acid (654) (2.39 g, 10.5 mmol), potassium persulfate (8.55 g, 31.6 mmol), cupric sulfate pentahydrate (2.62 g, 10.5 mmol) and acetonitrile/water (1:1) (90 mL) were heated at reflux for 1 hour. Ethyl acetate and water were added and the layers separated. The aqueous phase was extracted with ethyl acetate and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to provide 5-chloro-2,2-dimethyl-3-oxo-2,3-dihydrobenzofuran-7-carboxylic acid (655) as a yellow solid.

Workup

  1. temperatureat reflux for 1 hour
  2. customthe layers separated
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialthe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-35e4a2af12754a1191bac5f50a0428a9
Source dataset
uspto-grants-2012_11
Patent number
US08309600B2

Reaction notes

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