2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)acetamide → 5-oxo-5H-dibenzo[a,d]cyclohepten-2-acetic acid

Reaktionsgleichung

C(Cl)(Cl)Cl.CCCCCC.[CH:11]1[C:21]2[CH:20]=[CH:19][C:18]3[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=3[C:16](=[O:26])[C:15]=2[CH:14]=[CH:13][C:12]=1[CH2:27][C:28](N)=[O:29].CC(C)=[O:33].CCCCCC>>[CH:11]1[C:21]2[CH:20]=[CH:19][C:18]3[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=3[C:16](=[O:26])[C:15]=2[CH:14]=[CH:13][C:12]=1[CH2:27][C:28]([OH:29])=[O:33]

Komponenten

Edukt 3

HCID 204595902-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)acetamide

HCID 21585165Chloroform hexane

HCID 21880519Acetone hexane

Produkt 1

HCID 123988215-oxo-5H-dibenzo[a,d]cyclohepten-2-acetic acid

Versuchsvorschrift

3.0 Gm. of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)propionamide is refluxed in a mixture of 20 ml. of acetic acid and 30 ml. of concentrated hydrochloric acid for 3 hours. The solution is cooled and poured into water. The mixture is extracted with ethyl acetate and the extract is washed, dried and evaporated to yield 90% of 2-(5H-dibenzo[a,d] cyclohepten-5-on-2-yl)propionic acid., m.p. (chloroform-hexane) 138°-139°C.; m.p. (acetone-hexane) 113°-115°C. Use of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)acetamide gives a similar yield of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)acetic acid, m.p. (acetone-hexane) 148°-149.5°C.