HuagongsheHuagongshe Chemistry Print Report · For research reference only
Isopropanol → 3-Methoxy-5-(propan-2-yloxy)aniline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Isopropanol | HCID 3776 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | ethyl N-ethoxycarbonyliminocarbamate | HCID 220568 | — |
| Reactant | 3-Amino-5-methoxyphenol | HCID 11953516 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 3-Methoxy-5-(propan-2-yloxy)aniline | HCID 11571905 | 58.3% |
Reaction Steps
To a solution of 3-amino-5-methoxyphenol (5.44 g, 39.1 mmol), isopropyl alcohol (3.6 ml, 47 mmol) and triphenylphosphine (12.0 g, 47 mmol) in THF, was added diethyl azodicarboxylate (7.4 ml, 47 mmol). The reaction mixture was stirred for 16 h and the solvent was removed. The residue was purified by flash chromatography on silica gel eluting with 20% EtOAc/hexanes to afford the title compound (4.13 g). MS m/z: 182 [M+H]+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08765779B2 |
| Source dataset | uspto-grants-2014_07 |
| ORD ID | ord-689972f5ed864150a37c67ba9247ea6a |
| Source note | uspto-grants-2014_07 |