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

HRID 2058413Notes

Reaction equation

HRID 2058413 reaction equation
[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

Participants

6

Reactant 5

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

Product 1

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

Procedure

4-(p-Chlorophenyl)phenol is converted via the Duff reaction [J. Chem. Soc., 547 (1941)] to 2-hydroxy-5-(p-chlorphenyl)benzaldehyde, mp. 74°-78° C. i.r. 6.02μ. A solution of 233 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.

Workup

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

Sources & evidence

ORD record
ord-1fd1b8ca74924553ad635e204b8009f7
Source dataset
uspto-grants-1982_03
Patent number
US04317774

Reaction notes

Loading…