HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethylene Glycol → [2-(benzylamino)phenyl]methanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethylene Glycol | HCID 174 | — |
| Reactant | Benzylamine | HCID 7504 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 2-Iodobenzylic alcohol | HCID 107629 | — |
| 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 | [2-(benzylamino)phenyl]methanol | HCID 296053 | 95.2% |
Reaction Steps
The general procedure under argon was followed using copper(I) iodide (10 mg, 0.5 mmol), K3PO4 (425 mg, 2.00 mmol), benzylamine (131 μL, 1.20 mmol), 2-iodobenzylalcohol (234 mg, 1.00 mmol), ethylene glycol (111 μL, 2.00 mmol) and 2-propanol (1.0 mL). Column chromatography using a solvent mixture (hexane/ethyl acetate=4/1, Rf=0.3) afforded 2-(N-benzyl)aminobenzylalcohol (203 mg, 95% isolated yield) as off-white solid. The spectral data (1H NMR) matched with the literature references and GC analysis indicated >95% purity. See Coppola, G. A. J Herterocyl. Chem. 1986, 23, 223-224.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09067955B2 |
| Source dataset | uspto-grants-2015_06 |
| ORD ID | ord-194484b9d389452592f043b45548a234 |
| Source note | uspto-grants-2015_06 |