Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Iodide | HCID 4875 | — |
| Reactant | 4-tert-Butylphenol | HCID 7393 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 54515270 | HCID 54515270 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 131711343 | HCID 131711343 | 95.6% |
Reaction Steps
To a solution of 2.36 g of p-t-butylphenol in 3 ml of tetrahydrofuran is added 0.625 g of sodium hydride (60% dispersion in oil). After stirring under argon for 1 hour and heating at 50° C. for 20 minutes, 2.4 g of potassium iodide and 6.0 g of methyl bromo{p-[2-(p-chlorophenoxy)-1-methylethoxy]phenyl}acetate in 30 ml of tetrahydrofuran is added. The mixture is stirred and refluxed for 18 hours and poured into 300 ml of ice-water containing 3 ml of acetic acid. The mixture is extracted with dichloromethane and the extracts washed with saturated NaHCO3, 10% sodium thiosulfate and saturated sodium chloride solution. The dichloromethane extract is dried (MgSO4) and the solvent removed under reduced pressure to give 6.7 g of product as a gum. Chromatography over silica gel with dichloromethane as eluent gives 5.7 g of yellow gum.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04125732 |
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| Source dataset | uspto-grants-1978_11 |
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| ORD ID | ord-4a4b4883fcec4168991097e4ea161bcb |
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| Source note | uspto-grants-1978_11 |
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