Acetic Acid → 5H-Dibenzo(a,d)cycloheptene-2-acetic acid, alpha-methyl-5-oxo-

HRID 1576187Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1576187
C1CO[C:3]2([C:9]3[CH:10]=[CH:11][C:12]([CH:14]([CH3:18])[C:15](N)=[O:16])=[CH:13][C:8]=3[CH:7]=[CH:6][C:5]3[CH:19]=[CH:20][CH:21]=[CH:22][C:4]2=3)[O:2]1.Cl.C(O)(=[O:28])C>>[CH:13]1[C:8]2[CH:7]=[CH:6][C:5]3[CH:19]=[CH:20][CH:21]=[CH:22][C:4]=3[C:3](=[O:2])[C:9]=2[CH:10]=[CH:11][C:12]=1[CH:14]([CH3:18])[C:15]([OH:16])=[O:28]

Komponenten

4

Edukt 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 214030982-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)propionamide

Produkt 1

HCID 1739105H-Dibenzo(a,d)cycloheptene-2-acetic acid, alpha-methyl-5-oxo-Ausbeute 70 %

Versuchsvorschrift

11.0 Gm. of 2-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)propionamide is refluxed for 2 hours in 70 ml. of acetic acid and 105 ml. of concentrated hydrochloric acid. The mixture is cooled and diluted, then extracted with ether. The ethereal solution is extracted with aqueous sodium carbonate and the extract acidified and extracted with ethyl acetate to afford a 70% yield 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-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-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.

Aufarbeitung

  1. temperatureThe mixture is cooled
  2. additiondiluted
  3. extractionextracted with ether
  4. extractionThe ethereal solution is extracted with aqueous sodium carbonate
  5. extractionextracted with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-fd87f389a8964a9ebde347dff5a38673
Quelldatensatz
uspto-grants-1976_09
Patentnummer
US03979430

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