HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 5-Chloro-2-(3-hydroxyphenoxy)benzonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Resorcinol | HCID 5054 | — |
| Reactant | Potassium Hydroxide | HCID 14797 | — |
| Reactant | 2,5-Dichlorobenzonitrile | HCID 89000 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | 5-Chloro-2-(3-hydroxyphenoxy)benzonitrile | HCID 20495176 | 67.3% |
Reaction Steps
66 g of resorcinol are added to 220 ml of dimethyl sulphoxide. With stirring, 37.4 g of potassium hydroxide (powder) are added, whereupon the temperature rises to 55° C. The mixture is kept for 30 minutes at 60° C. and the 51.6 g of 2,5-dichlorobenzonitrile are added in portions. The reaction mixture is then stirred for 7 hours at 90° C. and, after cooling, poured into ice-water. The pH is adjusted to 6 with conc. hydrochloric acid and initially a brown oil precipitates, which soon becomes crystalline. Crystallisation from ethanol/-water yields 49.6 g of 3-(2'-cyano-4'-chlorophenoxy)-phenol with a melting point of 118°-120° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04394327 |
| Source dataset | uspto-grants-1983_07 |
| ORD ID | ord-3a00aab288f8408e9538f02bac6d9d3e |
| Source note | uspto-grants-1983_07 |