Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Methanol | HCID 887 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 58755241 | HCID 58755241 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 23111791 | HCID 23111791 | 55.1% |
Reaction Steps
To a solution of methyl (6-{[3-(2-methyl-1-naphthyl)benzyl]oxy}-2,3-dihydro-1-benzofuran-3-yl)acetate (0.801 g, 1.90 mmol) in a mixed solvent of methanol (6 mL) and tetrahydrofuran (6 mL) was added 2 M aqueous sodium hydroxide solution (3 mL), and the mixture was stirred at room temperature for 20 hr. Water was added to the reaction mixture, and the mixture was acidified with 1 M hydrochloric acid and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (30% ethyl acetate/hexane-ethyl acetate), and recrystallized from ethyl acetate-hexane to give the title compound (0.444 g, yield 55%) as colorless needle crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07820837B2 |
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| Source dataset | uspto-grants-2010_10 |
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| ORD ID | ord-d4e2337e89744542953fcf32833c6537 |
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| Source note | uspto-grants-2010_10 |
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