5-(3-METHYLPHENYL)-2-FUROIC ACID synthesis

5synthesis methods

Product Name:5-(3-METHYLPHENYL)-2-FUROIC ACID
CAS Number:400744-57-2
Molecular formula:C12H10O3
Molecular Weight:202.21

2-Furancarboxylic acid, 5-(3-methylphenyl)-, methyl ester

852145-99-4
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400744-57-2
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Yield:400744-57-2 88%

Reaction Conditions:

with sodium hydroxide in tetrahydrofuran;water at 0 - 20;Inert atmosphere;

Steps:

Generalprocedure for the synthesis of 58a-l, 59, 60, 61

General procedure: To a stirred solution of the appropriate methyl ester 54a-l, 55, 56, 57 (1.0 equiv) in THF (0.3 M) a 1.5 M aqueous solution of NaOH(1.5 equiv), except for 54i a 2.5 Maqueous solution of LiOH (4.0 equiv), was added dropwise at 0 °C. The resultingmixture was stirred at rt overnight (48 h for 54i). Afterward, the reaction was concentrated under reduced pressureand the aqueous residue was cooled at 0 °C and acidified to pH 1-2by dropwise addition of 2 M HCl aqueous solution. The resulting solidprecipitate was collected by vacuum filtration (except for compound 58l which was extracted from the waterphase with CH₂Cl₂/i-PrOH4:1). The obtained carboxylic acids 58a-l,59, 60, 61 were dried under reduced pressure and used for the nextreaction step without further purification

References:

Pismataro, Maria Chiara;Horenstein, Nicole A.;Stokes, Clare;Quadri, Marta;De Amici, Marco;Papke, Roger L.;Dallanoce, Clelia [European Journal of Medicinal Chemistry,2020,vol. 205,art. no. 112669] Location in patent:supporting information

2527-99-3 Synthesis