Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Iodoethane | HCID 6340 | — |
| Reactant | Potassium Hydroxide | HCID 14797 | — |
| Reactant | 2-Hydroxy-3-methyl-2-phenylbutanoic acid | HCID 12296639 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 15450552 | HCID 15450552 | 78.7% |
Reaction Steps
To a solution of 2-hydroxy-3-methyl-2-phenylbutanoic acid (Compound (5), 30.0 g) in dimethyl sulfoxide (250 ml) was added 85% powdered potassium hydroxide (60 g) and the mixed solution was stirred for one hour. Under ice cooling, ethyl iodide (55 ml) was added and the resulting mixture was stirred at room temperature for 3 days. After the addition of water (100 ml), the resulting mixture was stirred at 80° C. for 6 hours. The reaction mixture was acidified with 1N hydrochloric acid, followed by extraction with ether. The ether layer was dried over anhydrous sodium sulfate and removed under reduced pressure. To the residue, hexane (200 ml) was added. After the resulting mixture was allowed to stand overnight, the crystals so precipitated were removed by filtration. The filtrate was removed under reduced pressure to obtain the title compound (27.0 g, 78.7%) as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06060485 |
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| Source dataset | uspto-grants-2000_05 |
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| ORD ID | ord-6256b498b45b46ce90997be748c12be9 |
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| Source note | uspto-grants-2000_05 |
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