Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | HCID 86761270 | HCID 86761270 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 25128239 | HCID 25128239 | 82.7% |
Reaction Steps
600 mg (1.25 mmol) of methyl 3-{3-butoxy-4-[3-(4-methanesulfonyloxy-3-methoxyphenyl)propyl]phenyl}propanoate are dissolved in 10 ml of tetrahydrofuran and 1.8 ml (1.8 mmol) of aqueous 1N lithium hydroxide solution are then added. The reaction medium is stirred for 15 hours at room temperature. After addition of water and acidification with acetic acid, the reaction medium is extracted with ethyl acetate. The organic phases are combined, dried over sodium sulfate, filtered and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with an 8/2 heptane/ethyl acetate mixture. 480 mg (82%) of 3-{3-butoxy-4-[3-(4-methanesulfonyloxy-3-methoxyphenyl)propyl]phenyl}propanoic acid are obtained after crystallization from a 2/8 isopropyl ether/pentane mixture.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07879907B2 |
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| Source dataset | uspto-grants-2011_02 |
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| ORD ID | ord-dca7d388e52c48fc9649ca8ccadca6f8 |
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| Source note | uspto-grants-2011_02 |
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