1-benzofuran-3-carboxylic acid Chemical Properties

Melting point:

162℃

Boiling point:

325.6±15.0 °C(Predicted)

Density 

1.363±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

solid

pka

3.19±0.10(Predicted)

color 

White

InChI

InChI=1S/C9H6O3/c10-9(11)7-5-12-8-4-2-1-3-6(7)8/h1-5H,(H,10,11)

InChIKey

BENJFDPHDCGUAQ-UHFFFAOYSA-N

SMILES

O1C2=CC=CC=C2C(C(O)=O)=C1

Safety Information

HS Code 

2932990090

1-benzofuran-3-carboxylic acid Usage And Synthesis

Synthesis

The general procedure for the synthesis of benzofuran-3-carboxylic acid from 3-(methoxymethylenyl)-2(3H)-benzofuranone was as follows: 152 g of o-hydroxyphenylacetic acid was added to a reaction flask, 500 g of acetic anhydride and 250 g of trimethyl orthoformate were added. The temperature of the reaction mixture was raised to 80-100 °C and the temperature was maintained for 6 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure to give a yellow solid product. To this solid product, 500 g of methanol was added, stirred until completely dissolved, the temperature of the solution was controlled at 0-10 °C, and 180 g of 30% sodium hydroxide solution was slowly added dropwise. Subsequently, the reaction mixture was heated to 50-60°C and kept at this temperature for 3-6 hours. At the end of the reaction, methanol was recovered by distillation under reduced pressure. To the residue, 300 g of drinking water was added, the temperature of the solution was adjusted to below 30 °C, and 160 g of 30% hydrochloric acid was added slowly and dropwise to adjust the pH to 1-2. The mixture was cooled to 0-10 °C and allowed to stand for 3 hours for decantation. The precipitate was collected by filtration and the solid product was washed with cold water. Finally, the product was dried under vacuum to give 158 g of white solid benzofuran-3-carboxylic acid in 97.5% yield.

References

[1] Patent: CN108239054, 2018, A. Location in patent: Paragraph 0009; 0015; 0016; 0018; 0020; 0022; 0024

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