Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 21350305 | HCID 21350305 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | MeOH tetrahydrofuran | HCID 21899815 | — |
| Product | HCID 18182605 | HCID 18182605 | 94.3% |
Reaction Steps
To a solution of 2-(4-(furan-2-yl)-phenyl)-2-methyl-propionic acid methyl ester (2.0 g, 8.2 mmol) (reference example 30a) in MeOH/THF (20 mL, 1/1) is added NaOH (2 mL, 6M). The resulting solution is stirred for 1 hour then heated to 65° C. and stirred at this temperature for 2 hours. The reaction mixture is then cooled and acidified (to pH 1) with hydrochloric acid (2 M). The resulting mixture is diluted with ether, washed with water and brine, dried over MgSO4 and concentrated to give 1.78 g of the title compound as a solid. 1H NMR (CDCl3) d 1.61 (s, 6H), 6.45 (dd, J 3, 2 Hz, 1H), 6.62 (d, J=3 Hz, 1H), 7.42 (m, 2H), 7.45 (d, J=2 Hz, 1H), 7.64 (m, 2H). MS (EI) m/z 230 (M+)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06541505B1 |
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| Source dataset | uspto-grants-2003_04 |
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| ORD ID | ord-e5dc483d59ff42a4b9e6ce97da87d3e7 |
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| Source note | uspto-grants-2003_04 |
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