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

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

Reactant 3

HCID 313Hydrochloric Acid

HCID 702Ethanol

HCID 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).