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

HRID 428158Notes

Reaction equation

HRID 428158 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-03324708abc640eb9bd92afdf5c1307f
Source dataset
uspto-grants-2001_11
Patent number
US06313160B1

Reaction notes

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