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

Safety Information

HS Code 

2918999090

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(78515-16-9)Related Product Information

• Basic Violet 1
• 4-Methoxybenzoic acid
• Acetonitrile
• Methyl 4-(bromomethyl)benzoate
• Kresoxim-methyl
• Methyl 2-bromobenzoate
• Methanol
• Methyl benzoate
• Paraquat dichloride
• Methylparaben
• Methyl 4-methylbenzoate
• 2-Methoxybenzoic acid
• Methyl methoxyacetate
• Methyl 4-cyanobenzoate
• Methyl acrylate
• Methyl acetate
• methyl 5-formyl-2-nitrobenzoate
• Methyl