HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethylene Glycol → Diphenylamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethylene Glycol | HCID 174 | — |
| Reactant | Aniline | HCID 6115 | — |
| Reactant | Iodobenzene | HCID 11575 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Solvent | Ethyl acetate hexane | HCID 21226206 | — |
| Product | Diphenylamine | HCID 11487 | 41% |
Reaction Steps
The general procedure under argon was followed using copper(I) iodide (10 mg, 0.05 mmol), K3PO4 (425 mg, 2.00 mmol), aniline (109 μL, 1.20 mmol), iodobenzene (112 μL, 1.00 mmol), ethylene glycol (111 μL, 2.00 mmol) and 2-propanol (1.0 mL) at 90° C. Column chromatography using a solvent mixture (hexane/ethyl acetate=5/1, Rf=0.4) afforded N-(phenyl)aniline (69 mg, 41% isolated yield) as light yellow solid. The spectral data (1H NMR) matched with the literature references and GC analysis indicated >95% purity.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09067955B2 |
| Source dataset | uspto-grants-2015_06 |
| ORD ID | ord-20f8567112c54247afa8becc27127251 |
| Source note | uspto-grants-2015_06 |