Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | HCID 59253984 | HCID 59253984 | — |
| Solvent | Sodium Hydroxide | HCID 14798 | — |
| Product | HCID 59253932 | HCID 59253932 | 71.9% |
Reaction Steps
A mixture of 2-(6-Methoxycarbonylmethoxy-naphthalen-2-yl)-propionic acid methyl ester 31 (23 grams, 76.16 mmol) in 4 N—NaOH solutions (230 mL) was heated on a water bath at 90° C. for 8 hours. The reaction mass was cooled to room temperature and the pH adjusted to 2 with concentrated hydrochloric acid. Crude 89 was filtered, dried, and recrystallized from a mixture of ethyl acetate:hexane (1:6) to give pure 89 (15 grams, 71.9%) as a white powder. Mp: 185-188° C. IH NMR (DMSO-d6) δ 1.54 (d, 3H, CH3), 3.80 (q, 1H, CH), 4.74 (s, 2H, OCH2), 7.08 (s, 1H, Ar), 7.22 (m, 1H, Ar), 7.42 (m, 1H, Ar), 7.66 (m, 3H, Ar).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08318973B2 |
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| Source dataset | uspto-grants-2012_11 |
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| ORD ID | ord-6a7076e4ead0450c9f4892e336fdccb6 |
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| Source note | uspto-grants-2012_11 |
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