HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 6-(p-Chlorophenyl)coumarin-3-carboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | 4'-Chloro-4-biphenylol | HCID 91589 | — |
| Reactant | 2,2-Diethylpropanedioate | HCID 6951563 | — |
| Reactant | 4'-Chloro-4-hydroxy[1,1'-biphenyl]-3-carbaldehyde | HCID 20099791 | — |
| Product | 6-(p-Chlorophenyl)coumarin-3-carboxylic acid | HCID 20529781 | — |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04317774 |
| Source dataset | uspto-grants-1982_03 |
| ORD ID | ord-1fd1b8ca74924553ad635e204b8009f7 |
| Source note | uspto-grants-1982_03 |