Synthetic Studies on the Benzofuran Derivatives. II. Reactions of Aromatic o-Hydroxyaldehyde Derivatives and Ethyl Bromomalonate
- 1 January 1957
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 30 (1) , 3-6
- https://doi.org/10.1246/bcsj.30.3
Abstract
2-Carbethoxy-4-hydroxy-5-carbomethoxycoumarone (V) and 2,2-dicarbethoxy-3-hydroxy-6-benzyloxycoumaran (XII) were synthesized respectively from 2,6-dihydroxy-3-carbomethoxybenzaldehyde (IV) or 4-benzyloxy-2-hydroxybenzaldehyde (X) and ethyl bromomalonate by the method of Tanaka for benzofuran synthesis. 2-Carbethoxy-4-hydroxy-5-carbomethoxycoumarone (V) was hydrolysed to 4-hydroxycoumarone-2,5-dicarboxylic acid (VI). This dibasic acid VI was decarboxylated in quinoline with copper powder into a mixture of karanjol (VIII) and karanjic acid (IX). 2,2-Dicarbethoxy-3-hydroxy-6-benzyloxy-coumaran (XII) was hydrolysed to 6-benzyloxycoumarone-2-carboxylic acid (XIII).This publication has 6 references indexed in Scilit:
- Synthetic Studies on the Benzofuran Derivatives. Part I. A New Synthesis of KaranjinBulletin of the Chemical Society of Japan, 1955
- The Rearrangement of 2-Acetyl- and 2-Benzoylcoumarone Oxime p-ToluenesulfonatesJournal of the American Chemical Society, 1955
- Dérivés de l'aldéhyde nitro‐4‐salicylique. 1re communication: la nitro‐6‐coumaroneHelvetica Chimica Acta, 1954
- Coumarones from o-Hydroxyaldehydes and Bromomalonic EsterJournal of the American Chemical Society, 1951
- Untersuchungen über die γ-substituierten Resorcin-Derivate. I. MitteilYAKUGAKU ZASSHI, 1939
- Synthesen von Cumaron‐2‐carbonsäuren und von Oxy‐cumaronenHelvetica Chimica Acta, 1935