Hydrochloric Acid → 5-oxo-5H-dibenzo[a,d]cyclohepten-2-acetic acid

HRID 1283670Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1283670
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([CH2:13][C:14]([O:16]CC)=[O:15])=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]2[CH:19]=[CH:20][CH:21]=[CH:22][C:3]1=2.Cl>[OH-].[K+]>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([CH2:13][C:14]([OH:16])=[O:15])=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]2[CH:19]=[CH:20][CH:21]=[CH:22][C:3]1=2

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 53675848ethyl (5-oxo-5H-dibenzo[a,d]cyclohepten-2yl)acetate

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14797Potassium HydroxideLösungsmittel

Versuchsvorschrift

22 G. of 5-oxo-5H-dibenzo[a,d]cycloheptene-2-carboxylic acid is stirred in 200 ml. of chloroform, 50 ml. of thionyl chloride and 1 ml. of dimethylformamide for 8 hrs. The mixture is evaporated to dryness and the residue recrystallized from acetonitrile to yield 2-chloroformyl-5-oxo-5H-dibenzo[a,d]cycloheptene. This is dissolved in 200 ml. of chloroform and added to a 3-fold excess of ethereal diazomethane at 0°C. The mixture is left at 0°C for 12 hrs. then evaporated to dryness. The residue is recrystallized from acetonitrile to yield 2-diazoacetyl-5-oxo-5H-dibenzo-[a,d]cycloheptene. The diazoketone is heated to reflux in 250 ml. of ethanol and a saturated triethylamine solution of 2 g. of silver benzoate is added slowly until gas evolution ceases. The solution is cooled, filtered and evaporated to yield ethyl (5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)acetate. This ester is refluxed in 5% aqueous potassium hydroxide for 12 hrs. The solution is cooled, acidified with dilute hydrochloric acid and extracted with ether. The ether extract is dried and evaporated to yield (5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)acetic acid which can be recrystallized from acetone-hexane (m.p 148°-149.5°C).

Aufarbeitung

  1. temperatureThe solution is cooled
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. customis dried
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-1292bb05b86c46bf81c7c9b1dd75be11
Quelldatensatz
uspto-grants-1976_08
Patentnummer
US03975540

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