3-HYDROXY-5-METHOXYBENZOIC ACID

3-HYDROXY-5-METHOXYBENZOIC ACID Property

Melting point:

202-203 °C

Boiling point:

394.7±27.0 °C(Predicted)

Density 

1.351±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

3.96±0.10(Predicted)

Appearance

White to off-white Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

3-HYDROXY-5-METHOXYBENZOIC ACID Chemical Properties,Usage,Production

Definition

ChEBI: 3-hydroxy-5-methoxybenzoic acid is a methoxybenzoic acid.

Synthesis

GENERAL METHOD: Methyl 3-hydroxy-5-methoxybenzoate (4.5 g, 16.7 mmol) was dissolved in methanol (30 mL) and 1M sodium hydroxide solution (60 mL, 60 mmol) was added under nitrogen protection. The reaction mixture was stirred at 45 °C for 1-2 h. The progress of the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction solution was acidified with 1 M hydrochloric acid (50 mL) and subsequently extracted with ethyl acetate (3 x 50 mL). The organic phases were combined, washed with distilled water (2 × 30 mL) and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give 3-hydroxy-5-methoxybenzoic acid (5a) as an off-white solid (4.02 g, 94% yield) with a melting point of 196-198 °C.1H NMR (400 MHz, acetone-d6) δ (ppm): 7.42-7.33 (5H, m, benzyl Ph), 7.21 (1H, dd, J = 2.4,1.2 Hz. H-2), 7.11 (1H, dd, J = 2.4,1.2Hz, H-6), 6.68 (1H, t, J = 2.4Hz, H-4), 5.07 (2H, s, benzyl CH2). The obtained 1H NMR spectrum is in agreement with data reported in the literature [38].

References

[1] European Journal of Medicinal Chemistry, 2013, vol. 63, p. 415 - 422
[2] Journal of the American Chemical Society, 2005, vol. 127, # 6, p. 1737 - 1743
[3] Acta Phytochimica, 1939, vol. 11, p. 167,179
[4] Acta Phytochimica, 1939, vol. 11, p. 167,179