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

HRID 66933

反応式

HRID 66933 の反応式
[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

参加物

6

反応物 5

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

生成物 1

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

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-4cacc45e26214cf3858809b96f7c81c9
出典データセット
uspto-grants-1982_08
特許番号
US04343938

関連ノート

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