Hydrochloric Acid → 6-(p-Chlorophenyl)coumarin-3-carboxylic acid

HRID 66933

Reaktionsgleichung

Reaktionsgleichung von HRID 66933
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.OC1C=CC(C2C=CC(Cl)=CC=2)=CC=1C=O.[CH2:31]([C:33](CC)([C:37]([O-])=[O:38])[C:34]([O-:36])=[O:35])C.N1CCCCC1.Cl>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[C:12]3[C:11](=[CH:10][CH:9]=2)[O:14][C:37](=[O:38])[C:33]([C:34]([OH:36])=[O:35])=[CH:31]3)=[CH:6][CH:7]=1

Komponenten

6

Edukt 5

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 915894'-Chloro-4-biphenylolHCID 69515632,2-DiethylpropanedioateHCID 200997914'-Chloro-4-hydroxy[1,1'-biphenyl]-3-carbaldehyde

Produkt 1

HCID 205297816-(p-Chlorophenyl)coumarin-3-carboxylic acid

Versuchsvorschrift

4-(p-Chlorophenyl)phenol is converted via the Duff reaction [J. Chem. Soc., 547 (1941)] to 2-hydroxy-5-(p-chlorophenyl)benzaldehyde, mp. 74°-78° C. i.r. 6.02μ. A solution of 2]3 mg. (1 mmole) of this aldehyde, 0.4 ml. (2.63 mmole) of diethylmalonate and 0.2 ml. (2 mmole) of piperidine is heated for 10 minutes and kept at 25° C. for 2 hours. Then 5 ml. of 9 N HCl is added and the mixture stirred at reflux overnight. The mixture is cooled in an ice bath and filtered to yield 238 mg. of the desired compound, i.r. 5.74, 5.9μ.

Aufarbeitung

  1. temperatureat reflux overnight
  2. temperatureThe mixture is cooled in an ice bath
  3. filtrationfiltered
  4. customto yield 238 mg

Quellen und Nachweise

ORD-Eintrag
ord-4cacc45e26214cf3858809b96f7c81c9
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04343938

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