HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-(4-Cyano-2-ethyl-6-methyl-phenyl)-propionic acid ethyl ester → 3-(4-Cyano-2-ethyl-6-methylphenyl)propionic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-(4-Cyano-2-ethyl-6-methyl-phenyl)-propionic acid ethyl ester | HCID 66932084 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Sodium Hydroxide | HCID 14798 | — |
| Product | 3-(4-Cyano-2-ethyl-6-methylphenyl)propionic acid | HCID 57437414 | 84% |
Reaction Steps
A solution of 3-(4-cyano-2-ethyl-6-methyl-phenyl)-propionic acid ethyl ester (55.0 g, 224 mmol) in THF (220 mL) and 1N aq. NaOH solution (220 mL) is stirred at rt for 2 before it is diluted with water (200 mL) and extracted with DCM (2×200 mL). The aqueous phase is added to 32% aq. HCl solution (50 mL) at 15-30° C. A precipitate forms. The solid material is collected, washed with water and dried under high vacuum to give 3-(4-cyano-2-ethyl-6-methyl-phenyl)-propionic acid (40.87 g) as pale brown crystals; 1H NMR (D6-DMSO): δ 1.17 (t, J=7.5 Hz, 3H), 2.30-2.39 (m, 5H), 2.67 (q, J=7.3 Hz, 2H), 2.87-2.94 (m, 2H), 7.47 (s, 2H), 12.30 (s, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08288554B2 |
| Source dataset | uspto-grants-2012_10 |
| ORD ID | ord-069e2f09feb74cf5ae09cdc994d70150 |
| Source note | uspto-grants-2012_10 |