Ethanol → Ethyl 7-acetyl-2,3-dihydro-1,4-benzodioxine-2-carboxylate

HRID 1756027Notes

Reaction equation

HRID 1756027 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][CH:10]([C:13](N)=[O:14])[O:9][C:8]=2[CH:16]=1)(=[O:3])[CH3:2].[CH2:17]([OH:19])[CH3:18]>Cl>[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][CH:10]([C:13]([O:19][CH2:17][CH3:18])=[O:14])[O:9][C:8]=2[CH:16]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 702EthanolHCID 181774107-Acetyl-2,3-dihydro-1,4-benzodioxin-2-carboxamide

Product 1

HCID 13723676Ethyl 7-acetyl-2,3-dihydro-1,4-benzodioxine-2-carboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Heat a solution of 3 g (13.5 mmol) of 7-acetyl-2,3-dihydro-1,4-benzodioxin-2-carboxamide dissolved in 100 cm3 of ethanol saturated with hydrochloric acid at reflux for 18 hours under a nitrogen atmosphere. After cooling, the reaction mixture is filtered, concentrated and, after neutralisation with sodium hydrogen carbonate, extracted with methylene chloride. The crude product obtained by concentrating the organic phase to dryness is purified by chromatography on a silica column (eluant: petroleum ether/diethyl ether, 50:50). Ethyl 7-acetyl-2,3-dihydro-1,4-benzodioxin-2-carboxylate is thereby obtained in a yield of 75%. Melting point: 57° C. ##STR35##

Workup

  1. temperatureat reflux for 18 hours under a nitrogen atmosphere
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture is filtered
  4. concentrationconcentrated
  5. extractionafter neutralisation with sodium hydrogen carbonate, extracted with methylene chloride
  6. customThe crude product obtained
  7. concentrationby concentrating the organic phase to dryness
  8. customis purified by chromatography on a silica column (eluant: petroleum ether/diethyl ether, 50:50)

Sources & evidence

ORD record
ord-848e28a70b944e00ad18b80de5892a22
Source dataset
uspto-grants-1995_08
Patent number
US05439909

Reaction notes

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