HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → Methyl 4-(3-hydroxyprop-1-ynyl)benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Propargyl alcohol | HCID 7859 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methyl 4-iodobenzoate | HCID 69273 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | Methyl 4-(3-hydroxyprop-1-ynyl)benzoate | HCID 4448596 | 87.5% |
Reaction Steps
To a solution of methyl 4-iodobenzoate (20 g, 76 mmol), propargyl alcohol (5.55 g, 99.0 mmol) and triethylamine (20 mL) in acetonitrile (200 mL) was added dichlorobis(triphenylphosphine)palladium(II) (1.55 g, 2.21 mmol), followed by CuI (454 mg, 2.38 mmol). The reaction mixture was stirred at room temperature for 24 h. Water was added and the aqueous solution was washed with EtOAc (3×). The organic solutions were combined, dried (MgSO4), filtered and concentrated. Purification by medium pressure chromatography (9:1 hexanes:EtOAc to 4:1 hexanes:EtOAc) provided 4-(3-hydroxy-prop-1-ynyl)-benzoic acid methyl ester (12.65 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07414071B2 |
| Source dataset | uspto-grants-2008_08 |
| ORD ID | ord-50e845f8094c4518af8574dcfdd80d2c |
| Source note | uspto-grants-2008_08 |