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

HRID 37158Notes

Reaction equation

HRID 37158 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>C(Cl)Cl>[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-carboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Heat a solution of 2 g (8 mmol) of ethyl 7-acetyl-2,3-dihydro-1,4-benzodioxin-2-carboxylate and 3.05 g (17.7 mmol) of meta-chloro-perbenzoic acid in 30 cm3 of methylene chloride at 50° C. for 18 hours under a nitrogen atmosphere. After cooling, removing by filtration the benzoic acid formed, and washings with aqueous solutions of sodium hydrogen carbonate and then sodium chloride, the reaction mixture is concentrated to dryness under reduced pressure and the crude product obtained is purified by chromatography on a silica column (eluant:petroleum ether/diethyl ether, 70:30). Ethyl 7-acetoxy-2,3-dihydro-1,4-benzodioxin-2-carboxylate is thereby obtained in a yield of 75%. ##STR34##

Workup

  1. temperatureAfter cooling
  2. customremoving by filtration the benzoic acid
  3. customformed
  4. washwashings with aqueous solutions of sodium hydrogen carbonate
  5. concentrationsodium chloride, the reaction mixture is concentrated to dryness under reduced pressure
  6. customthe crude product obtained
  7. customis purified by chromatography on a silica column (eluant:petroleum ether/diethyl ether, 70:30)

Sources & evidence

ORD record
ord-ba1d433d8c5348008b97418b1f2f6163
Source dataset
uspto-grants-1995_05
Patent number
US05420132

Reaction notes

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