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| | Methyl 5-formyl-2-methoxybenzoate Basic information |
| | Methyl 5-formyl-2-methoxybenzoate Chemical Properties |
| Melting point | 86-87 °C | | Boiling point | 163-165 °C(Press: 1 Torr) | | density | 1.191±0.06 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | Appearance | White to off-white Solid | | InChI | InChI=1S/C10H10O4/c1-13-9-4-3-7(6-11)5-8(9)10(12)14-2/h3-6H,1-2H3 | | InChIKey | CNRMXICSYWVJRD-UHFFFAOYSA-N | | SMILES | C(OC)(=O)C1=CC(C=O)=CC=C1OC |
| | Methyl 5-formyl-2-methoxybenzoate Usage And Synthesis |
| Chemical Properties | White to Almost white powder to crystaline; Melting Point 87 °C. | | Uses | Methyl 5-Formyl-2-methoxybenzoate is an intermediate used to synthesize peroxisome proliferator-activated receptor (PPAR) activators. It is also used to prepare 1,4-bis(3-hydroxycarbonyl-4-hydroxyl)styrylbenzene derivatives as PTP1B inhibitors. | | Synthesis | General procedure for the synthesis of methyl 5-formyl-2-methoxybenzoate from 5-formyl-2-hydroxybenzoic acid and iodomethane: 5-formyl-2-hydroxybenzoic acid (2.0 g, 12.0 mmol), iodomethane (1.5 mL, 25 mmol) and potassium carbonate (3.06 g, 22.2 mmol) were mixed in dimethylformamide (15 mL). The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The crude product was dissolved in ethyl acetate, washed sequentially with water (2×), saturated saline (2×) and the organic phase was dried with anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure and the resulting residue was purified by column chromatography to afford the target product methyl 5-formyl-2-methoxybenzoate 1.85 g (79% yield). The structure of the product was confirmed by 1H-NMR (CDCl3, 500 MHz) and mass spectrometry: 1H-NMR δ 9.91 (s, 1H), 8.31 (d, J = 2.1 Hz, 1H), 8.02 (dd, J = 8.5, 2.5 Hz, 1H), 7.11 (d, J = 8.6 Hz, 1H), 3.99 (s, 3H), 3.91 (s, 3H); mass spectrometry: 195 (s, 3H); mass spectrometry: 196 (s, 3H); mass spectrometry: 196 (s, 3H). 3H); MS: 195.05 (MH)+. | | References | [1] Patent: US2007/249607, 2007, A1. Location in patent: Page/Page column 65; 67; 69
[2] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 2, p. 313 - 316
[3] European Journal of Medicinal Chemistry, 2004, vol. 39, # 7, p. 573 - 578
[4] Patent: WO2014/202580, 2014, A1. Location in patent: Page/Page column 114
[5] Patent: WO2014/202528, 2014, A1. Location in patent: Page/Page column 108; 109 |
| | Methyl 5-formyl-2-methoxybenzoate Preparation Products And Raw materials |
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