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

HRID 66933

반응식

HRID 66933 반응식
[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

참가 물질

6

반응물 5

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

생성물 1

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

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-4cacc45e26214cf3858809b96f7c81c9
출처 데이터셋
uspto-grants-1982_08
특허 번호
US04343938

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