HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzene → 5-[2-(2,5-Dimethoxyphenyl)ethinyl]-2-hydroxybenzoic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzene | HCID 241 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methyl 5-Iodosalicylate | HCID 248910 | — |
| Reactant | 2,5-Dimethoxyphenylacetylene | HCID 11094951 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Oxygen | HCID 977 | — |
| Product | 5-[2-(2,5-Dimethoxyphenyl)ethinyl]-2-hydroxybenzoic acid methyl ester | HCID 15384006 | — |
Reaction Steps
Under argon atmosphere 240 mg of 2,5-dimethoxyphenylacetylene and 493 mg of methyl 5-iodosalicylate are dissolved in 20 ml of oxygen-free and dry benzene. The mixture is treated with 85 mg of tetrakis (triphenylphosphine)palladium, 20 mg of copper(I)iodide and 450 mg of triethylamine, stirred at room temperature overnight and then poured onto 100 ml of aqueous pH 7 buffer. After extraction with ethyl acetate and purification by chromatography on silicagel, 5-[2-(2,5-dimethoxyphenyl)ethinyl]-2-hydroxybenzoic acid methyl ester is obtained (colorless crystals of M.P. 105°-108°).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05488135 |
| Source dataset | uspto-grants-1996_01 |
| ORD ID | ord-00b5aedde9b640c795ea84266ba6a003 |
| Source note | uspto-grants-1996_01 |