Abstract
Abstract Methyl isobutyl ketone and phenylacetone, unlike methyl ethyl ketone, condensed with furfural by sodium hydroxide at their α-methyl groups irrespective of the reaction temperature, giving 1-(2-furyl)-5-methyl-1-hexen-3-one (III) and 4-(2-furyl)-1-phenyl-3-buten-2-one (V) respectively. 1-(2-Furyl)-5-methyl-1-hexen-3-one (III) gave the two forms of 2,4-dinitrophenylhydrazone. One (m.p. 145-146°) shifted readily to the other (m.p. 196-197°) in dilute alcoholic sulfuric acid, and those may be the syn- and anti-isomers. 4-(2-Furyl)-1-phenyl-3-buten-2-one (V) obtained here gave the two species of semi-carbazone which were converted into the respective two species of 2,4-dinitrophenylhydrazone. It may perhaps be composed of the cis- and trans-isomers. This furfurylidene ketone gave γ, ζ-dioxo-η-phenylcaprylic acid (VI) by the ring-opening in alcoholic hydrochloric acid.
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