2-HYDROXY-4,5-DIMETHOXY BENZOIC ACID Chemical Properties

Melting point:

213-214℃ (decomposition)

Boiling point:

361.5±42.0 °C(Predicted)

Density 

1.335±0.06 g/cm3(Predicted)

storage temp. 

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

pka

3.13±0.10(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C9H10O5/c1-13-7-3-5(9(11)12)6(10)4-8(7)14-2/h3-4,10H,1-2H3,(H,11,12)

InChIKey

RUBXSZYVSFYJQR-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC(OC)=C(OC)C=C1O

2-HYDROXY-4,5-DIMETHOXY BENZOIC ACID Usage And Synthesis

Uses

4,5-Dimethoxysalicylic Acid has been used as a reactant for the preparation of Salicylanilide derivatives as inhibitors of the protein tyrosine kinase epidermal growth factor receptor.

Synthesis

General procedure for synthesizing 2-hydroxy-4,5-dimethoxybenzoic acid from methyl 2-hydroxy-4,5-dimethoxybenzoate: sodium hydroxide (0.75 mol) and 100 mL of water were added to a reaction flask and stirred until clarified. Methyl 2-hydroxy-4,5-dimethoxybenzoate (0.25 mol) was suspended in the above alkaline solution according to the preparation method of Example 1 and stirred at room temperature for about 3.0 hours. The reaction progress was monitored by TLC, and after confirming the completion of the reaction, the reaction system was cooled to 10 °C, and the pH was adjusted slowly and dropwise to 4.0 by adding dilute hydrochloric acid.Subsequently, stirring, filtration, and drying were carried out, and 47.4 g of 2-hydroxy-4,5-dimethoxybenzoic acid was obtained, with a molar yield of 95.2% and a purity of 99.5% by HPLC.

References

[1] Patent: CN106316979, 2017, A. Location in patent: Paragraph 0044; 0045; 0046; 0047; 0048; 0049
[2] Journal of the American Chemical Society, 1942, vol. 64, p. 2983,2985

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