Reduction of Unsaturated Aliphatic Mono-and Dicarboxylic Acids and Brominated Aliphatic Acids with Raney Alloys in an Alkaline Solution, Affording the Corresponding Saturated Aliphatic Acids

概要

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The reduction of trans-2-pentenoic acid (1a), 4-pentynoic acid (5), and 2-bromopentanoic acid (6) with Ni-Al and Cu-Al alloys in 10% NaOH solution afforded the expected pentanoic acid (4) in good yields. Under the above conditions, trans-3-and 4-pentenoic acids, (2) and (3), were not reduced. But, the reduction in the presence of 10% Pd/C catalyst (43 weight % of the alloys) gave 4. In 10% Na_2CO_3 solution, the treatment of 5 with Cu-Al afforded pen-tenoic acid (3) as a major product. The reduction of 2,3-dibromopentanoic acid (8) gave 4 or a mixture of 4, la, and cis-2-pentenoic acid (1b) upon the conditions employed. Fumaric acid (10), maleic anhydride (11), and acety-lenedicarboxylic acid (12), and 2,3-dibromosuccinic acid (13) afforded the expected succinic acid (14) in 71-80%yields in the reduction with the alloys in 10% NaOH solution.
九州大学の論文
1988-12-28