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

HRID 972984Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 972984
[CH2:1]1COC2(C3C=CC(CC#N)=CC=3C=CC3C=CC=CC2=3)O1.Cl.[CH:24]1[C:34]2[CH:33]=[CH:32][C:31]3[CH:35]=[CH:36][CH:37]=[CH:38][C:30]=3[C:29](=[O:39])[C:28]=2[CH:27]=[CH:26][C:25]=1[CH2:40][C:41]([OH:43])=[O:42].C1COC2(C3C=CC(C(C)C#N)=CC=3C=CC3C=CC=CC2=3)O1>O.C(OCC)(=O)C.C(O)(=O)C>[CH:24]1[C:34]2[CH:33]=[CH:32][C:31]3[CH:35]=[CH:36][CH:37]=[CH:38][C:30]=3[C:29](=[O:39])[C:28]=2[CH:27]=[CH:26][C:25]=1[CH:40]([CH3:1])[C:41]([OH:43])=[O:42]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 123988215-oxo-5H-dibenzo[a,d]cyclohepten-2-acetic acidHCID 123988235,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl acetonitrileHCID 214031012-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)propionitrile

Produkt 1

HCID 1739105H-Dibenzo(a,d)cycloheptene-2-acetic acid, alpha-methyl-5-oxo-Ausbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

23.4 Gm. of 5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl acetonitrile is refluxed for 7 hours in 160 ml. of acetic acid and 240 ml. of concentrated hydrochloric acid. The solution is cooled and added to ethyl acetate and water. The organic layer is washed with water then extracted with aqueous sodium carbonate. The extract is acidified with hydrochloric acid and extracted with ethyl acetate. The extract is dried and evaporated to afford the product which is recrystallized from acetone/hexane to give 9.5 gm., 50%, of 5H-dibenzo[a,d]cyclohepten-5-on-2-yl acetic acid, m.p. 148°-149.5° C. Use of 2-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)propionitrile gives a 75% 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.

Aufarbeitung

  1. temperatureThe solution is cooled
  2. washThe organic layer is washed with water
  3. extractionthen extracted with aqueous sodium carbonate
  4. extractionextracted with ethyl acetate
  5. customThe extract is dried
  6. customevaporated
  7. customto afford the product which
  8. customis recrystallized from acetone/hexane
  9. customto give 9.5 gm

Quellen und Nachweise

ORD-Eintrag
ord-5fb0b6f640084994b32f2c3c7de341c5
Quelldatensatz
uspto-grants-1977_10
Patentnummer
US04054579

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