Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Phenol | HCID 996 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Methyl bromoacetate | HCID 60984 | — |
| Catalyst | Tetrabutylammonium Iodide | HCID 67553 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 10679746 | HCID 10679746 | — |
Reaction Steps
Methyl bromoacetate (0.56 mL, 5.92 mmol) is added to a solution of phenol (0.70 g, 5.29 mmol), K2CO3 (1.6 g, 11.6 mmol) and tetrabutyl ammonium iodide (0.57 g, 1.53 mmol) in 30 mL of DMF. The resulting solution is heated to 80° C. for 16 hours. The solution is then cooled to ambient temperatures. The solution is diluted with EtOAc. The resulting solution is washed with H2O and saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with a gradient of 10% EtOAc/hexanes to 50% EtOAc/hexanes to afford the title compound (1.4 g, 0.8 mmol).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05958918 |
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| Source dataset | uspto-grants-1999_09 |
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| ORD ID | ord-dc2e1ec6c62a40a1a9269904fa09f310 |
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| Source note | uspto-grants-1999_09 |
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