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Terpene compounds. Part IV. A synthesis of cis- and trans-(±)- isofenchocamphoric acid
R SWAMINATHAN, D MUKHERJI, J C BARDHAN
Published in -
1949
Pages: 192 - 195
Abstract
Ethyl 2:2:4-trimethylcyclohexan-1-one-4-carboxylate, the preparation of which is now described, affords, on bromination followed by treatment with barium hydroxide, 1-hydroxy-3:5:5-trimethylcyclopentane-1:3-dicarboxylic acid. The reaction involves molecular rearrangement of the type previously observed by Wallach, Simonsen, and their co-workers. The product is probably the trans-modification of Aschan's α-hydroxyisofenchocamphoric acid, since, on dehydration with phosphorus oxychloride and pyridine, it gives 3:5:5-trimethylcyclopent-1-ene-1:3-dicarboxylic acid (dehydroisofenchocamphoric acid). This on catalytic reduction gives (±)-cis-isofenchocamphoric acid, which establishes the correctness of Semmler-Wallach formula for this acid. A direct synthesis of dehydrosisofenchocamphoric acid from ethyl 2:2:4-trimethylcyclopentan-1-one-4-carboxylate (Bardhan and Ganguli, J., 1936, 1852) by the action of hydrogen cyanide followed by dehydration and hydrolysis is also described.
About the journal
JournalJournal of the Chemical Society (Resumed)
Publisher-
ISSN0368-1769