m-Chloroperbenzoic acid → Ethyl 7-acetoxy-2,3-dihydro-1,4-benzodioxin-2-carboxylate

HRID 394654Notes

Reaction equation

HRID 394654 reaction equation
C([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][CH:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[O:9][C:8]=2[CH:18]=1)(=O)C.ClC1C=CC=[C:22]([C:26]([O:28]O)=[O:27])C=1>ClCCl>[C:26]([O:28][C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][CH:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[O:9][C:8]=2[CH:18]=1)(=[O:27])[CH3:22]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13723676Ethyl 7-acetyl-2,3-dihydro-1,4-benzodioxine-2-carboxylate

Product 1

HCID 10858395Ethyl 7-acetoxy-2,3-dihydro-1,4-benzodioxin-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4 g (16 mmol) of the ester obtained in Step C are dissolved in 60 ml of anhydrous dichloromethane; 6.1 g (35.4 mmol) of meta-chloroperbenzoic acid are then added to the medium. After 18 hours of reflux under an inert atmosphere, the mixture is cooled and then hydrolysed with ice-cold water. The aqueous phase is extracted with dichloromethane; the organic phase is then washed several times with a saturated solution of sodium hydrogen carbonate. After drying over magnesium sulphate and evaporation of the solvent in vacuo, the residue obtained is purified on a silica column (eluant: AcOEt/PE: 30/70) to yield the title ester in the form of a syrup.

Workup

  1. temperatureAfter 18 hours of reflux under an inert atmosphere
  2. temperaturethe mixture is cooled
  3. extractionThe aqueous phase is extracted with dichloromethane
  4. washthe organic phase is then washed several times with a saturated solution of sodium hydrogen carbonate
  5. dry with materialAfter drying over magnesium sulphate and evaporation of the solvent in vacuo
  6. customthe residue obtained
  7. customis purified on a silica column (eluant: AcOEt/PE: 30/70)

Sources & evidence

ORD record
ord-87392282c6ba409fb6985b3e2da91b0d
Source dataset
uspto-grants-2003_08
Patent number
US06602903B2

Reaction notes

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