The Condensations of Furfural with Acetylacetone and Ethyl Propionylacetate
- 1 April 1954
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 27 (4) , 213-215
- https://doi.org/10.1246/bcsj.27.213
Abstract
3-Acetyl-4-(2-furyl)-3-buten-2-one (I) and ethyl α-propionyl-2-furanacrylate (V) were obtained by the condensations of furfural with acetylacetone and ethyl propionylacetate by piperidine, respectively. 3-Acetyl-4-(2-furyl)-3-buten-2-one (I) was oxidised by sodium hypochlorite to furfurylidenemalonic acid (II), and, on refluxing with alcohoric hydrochloric acid and subsequent hydrolysis, gave β-(4-acetyl-5-methyl-2-furyl)-propionic acid (IV). Ethyl α-propionyl-2-furanacrylate (V) gave γ,ζ-dioxopelargonic acid (VI) by refluxing with alcoholic hydrochloric acid and subsequent hydrolysis. The dioxocaboxylic acid (m. p. 83∼84°), obtained by the ring-opening of the furfurylidene ketone (b.p. 126°/19 mm.) in alcoholic hydrochloric acid which was considered to be 1-(2-furyl)-1-penten-3-one (VII) in the previous reports, was identical with this γ,ζ-dioxopelargonic acid (VI). It was confirmed, therefore, that the ideas in the previous reports6) was correct.This publication has 4 references indexed in Scilit:
- The Condensation of Furfural with Methyl Ethyl Ketone by Aqueous Sodium HydroxideBulletin of the Chemical Society of Japan, 1954
- On the Ring-opening Reactions of the Furan Compounds. III. On the Condensation of Furfural with Methyl Ethyl Ketone by AlkaliBulletin of the Chemical Society of Japan, 1953
- Some Aryl Substituted Cyclopentenones: A New Synthesis of the Cyclopentenophenanthrene StructureJournal of the American Chemical Society, 1949
- Ueber eine Darstellungsweise des BenzylidenacetessigestersEuropean Journal of Inorganic Chemistry, 1896