Uses
2,3-Dihydro-1,4-benzodioxin-2-carboxylic Acid Ethyl Ester is an intermediate used to prepare presynaptic α2-adrenoreceptor antagonists and potential antidepressants. It is also used to prepare aminoalkylbenzodioxins as calcium antagonists.
Synthesis Reference(s)
Journal of the American Chemical Society, 77, p. 5373, 1955
DOI: 10.1021/ja01625a050
Synthesis
GENERAL METHOD: A mixture of 12 g (0.11 mol) of catechol, 17.9 g (0.1 mol) of ethyl 2,3-dibromopropionate, and 41.4 g (0.3 mol) of anhydrous K2CO3 was refluxed for 18 hours in 200 mL of anhydrous acetone. Upon completion of the reaction, acetone was removed by distillation under reduced pressure and the residue was dissolved in dichloromethane. The organic phase was washed sequentially with water, 5% NaOH solution, 5% HCl solution and saturated NaCl solution and finally dried with anhydrous Na2SO4. After evaporating the solvent under reduced pressure, the residue was distilled to give 15.4 g (74% yield) of ethyl 1,4-benzodioxane-2-carboxylate.
References
[1] Sangita M. Kasture. “Novel enzymatic route for kinetic resolution of (±)1,4-benzodioxan-2-carboxylic acid.” Biochemical Engineering Journal 27 1 (2005): Pages 66-71.
