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

HRID 428157Notes

Reaction equation

HRID 428157 reaction equation
Cl.[C:2]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH2:12][CH:11]([C:14](N)=[O:15])[O:10][C:9]=2[CH:17]=1)(=[O:4])[CH3:3].[CH2:18]([OH:20])[CH3:19]>>[C:2]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH2:12][CH:11]([C:14]([O:20][CH2:18][CH3:19])=[O:15])[O:10][C:9]=2[CH:17]=1)(=[O:4])[CH3:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 181774107-Acetyl-2,3-dihydro-1,4-benzodioxin-2-carboxamide

Product 1

HCID 13723676Ethyl 7-acetyl-2,3-dihydro-1,4-benzodioxine-2-carboxylate

Procedure

150 ml of ethanol are saturated with hydrochloric acid; 6 g (27.12 mmol) of the amide obtained in Step B are then added to the medium. After 18 hours of reflux, the mixture is cooled and then filtered. The filtrate is concentrated in vacuo and the residue is taken up in water; the aqueous phase is then neutralised with solid sodium hydrogen carbonate. After extraction with dichloromethane, the organic phase is dried over magnesium sulphate, filtered and then concentrated in vacuo. The title ester is obtained in the form of a white solid after passage over a silica column (eluant:AcOEt/PE:30/70).

Workup

  1. temperatureAfter 18 hours of reflux
  2. temperaturethe mixture is cooled
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated in vacuo
  5. extractionAfter extraction with dichloromethane
  6. dry with materialthe organic phase is dried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b3940d21f08b4872b6f5f1cb2ecc31dc
Source dataset
uspto-grants-2001_11
Patent number
US06313160B1

Reaction notes

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