Green Synthesis of Acid Esters from Furfural via Stobbe Condensation

Abstract EN

Solvent-free Stobbe condensation of furfural 1 with dimethyl succinate 2 under anhydrous conditions at room temperature using dry-solid potassium tertiary butoxide gave 3-carbomethoxy, 4-furyl-3-butenoic acid 3, which upon methylation followed by Stobbe condensation reaction with different aldehydes and/or ketones under anhydrous conditions at room temperature afforded substituted carbomethoxy acids 5a–f.

These acid ester products were saponified to the corresponding dicarboxylic acids 6a–f which are useful in the synthesis of photochromic fulgides.