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Terpene compounds. Part VI. A synthesis of (±)-isofenchone
D MUKHERJI, J C BARDHAN
Published in -
1949
Pages: 197 - 199
Abstract
Ethyl 2 : 2 : 4-trimethylcyclopentan-1-one-4-carboxylate (Bardhan and Ganguli, J., 1936, 1853) condenses with ethyl cyanoacetate to give ethyl 4-carbethoxy-2 : 2 : 4-trimethylcyclopentylidenecyanoacetate. This is reduced catalytically to ethyl 4-carbethoxy-2 : 2 : 4-trimethylcyclopentylcyanoacetate, which on hydrolysis with hydrochloric acid gave 4-carboxy-2 : 2 : 4-trimethylcyclopentaneacetic acid. The last on pyrolysis yielded a ketone identical with (±)-isofenchone. On oxidation with potassium permanganate the synthetic ketone gives an excellent yield of (±)-cis- isofenchocamphoric acid. This synthesis supplies the final proof of the correctness of Semmler's formula for isofenchone.
About the journal
JournalJournal of the Chemical Society (Resumed)
Publisher-
ISSN0368-1769