Study of the synthesis of trans-cyclo-pentane-1,2-dicarboxylic acid Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/v692tb08w

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  • The object of this study is the synthesis of trans-cyclopentane-1, 2-dicarboxylic acid. Five procedures designed for the synthesis of this trans diacid are described in the literature. The procedure devised by Perkin in 1887, Fuson and Cole in 1938, and by Brenner in 1961 were investigated to determine which of these three offer the most practical method for the synthesis of trans-cyclopentane-1, 2 dicarboxylic acid. Perkins procedure appears to be the most promising and the most practical procedure for the preparation of this diacid. This procedure consists of a three-step reaction. The starting materials diethyl malonate and 1, 3-dibromopropane combine to form tetraethyl pentane-1, 1, 5, 5-tetracarboxylate. This tetra ester upon being cyclized is hydrolyzed in a final step to produce trans-cyclopentane-1, 2-dicarboxylic acid in a 7.4% yield. The crucial steps in this procedure are the first and third reactions. After a modification of these crucial steps trans-cyclopentane-1, 2-dicarboxylic acid was obtained in this laboratory in an over-all yield of 67%. The procedure of Fuson and Cole starting with pimelic acid gave an over-all yield of 57.1% for the trans diacid. This method, however, is much more tedious involving five separate reactions. Brenner's procedure starting with 2-carboethoxycyclohexanone gave trans-cyclopentane-1, 2-dicarboxylic acid in an over-all yield of 67.2%. This procedure is far less practical than Perkin's for making the trans diacid on a large scale due to experimental complications and the tedious isolation of the product.
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