ChemicalBook CAS DataBase List 4-Benzofurancarboxylic Acid

4-Benzofurancarboxylic Acid synthesis

6synthesis methods

Product Name:4-Benzofurancarboxylic Acid
CAS Number:166599-84-4
Molecular formula:C9H6O3
Molecular Weight:162.14

41019-56-1

166599-84-4

General procedure for the synthesis of benzofuran-4-carboxylic acid from methyl benzofuran-4-carboxylate: a solution of LiOH (1.44 g, 34.3 mmol) in water (20 mL) was added to a mixture of THF (20 mL) and MeOH (20 mL) of methyl benzofuran-4-carboxylate (2.02 g, 11.4 mmol) and the reaction was stirred at room temperature for 16 The reaction was stirred for 16 hours at room temperature. After completion of the reaction, the solvent was removed by evaporation. The residue was dissolved in water (50 mL) and acidified with concentrated HCl to pH < 2. The precipitate was collected by filtration and dried to afford benzofuran-4-carboxylic acid (1.83 g, 99% yield). The product was characterized by 1H NMR (DMSO-d6): δ 13.10 (s, 1H), 8.14 (d, J = 2.1 Hz, 1H), 7.85-7.91 (m, 2H), 7.43 (t, J = 7.9 Hz, 1H), 7.33 (dd, J = 2.1, 1.0 Hz, 1H). Mass spectrum measured value: [M-H]? = 161.1.

41019-56-1 Synthesis

41019-56-1
45 suppliers
$60.00/100mg

166599-84-4
105 suppliers
$63.00/100mg

Yield: 99%

Reaction Conditions:

with water;lithium hydroxide in tetrahydrofuran;methanol at 20; for 16 h;

Steps:

Benzofuran-4-caroxylic acid (132)
A solution of LiOH (1.44 g, 34.3 mmol) in water (20 mL) was added to a solution of 131 (2.02 g, 11.4 mmol) in THF (20mL) and MeOH (20 mL) and the solution was stirred at r.t. for 16 h and then evaporated. The residue was dissolved in water (50 mL) and acidified with cone. HC1 and the precipitate was filtered and dried to give 132 (1.83 g, 99%). 1H NMR (DMSO-d₆) δ 13.10 (s, 1H), 8.14 (d, J = 2.1 Hz, 1H), 7.85-7.91 (m, 2H), 7.43 (t, J = 7.9 Hz, 1H), 7.33 (dd, J = 2.1, 1.0 Hz, 1H). Found: [M-H] = 161.1.

References:

THE GLOBAL ALLIANCE FOR TB DRUG DEVELOPMENT, INC.;UPTON, Anna, Marie;COOPER, Christopher, Blair;MARCEL, Koenraad, Jozel Lodewijk;GUILLEMONT, Jerome, Emile Goerges;VAN DEN BROECK, Walter Marcel, Mathilde;PALMER, Brian, Desmond;MA, Zhenkun WO2017/155909, 2017, A1 Location in patent:Paragraph 0190