Quantitative Relationships in the Reactions of trans-4-X-Cyclohexanecarboxylic Acids and their Methyl Esters¹

Bioconversion of Dinitrile to Mononitrile, a Tranexamic Acid Intermediate, byCorynebacteriumsp.

“…2 ) The Rf values on thin-layer chromatography and the melting point 8 ) of the product well coincided with those of t-MCC. The infrared spectrum of the esterified derivative of the product well coincided with that of authentic t-MCC.…”

The influence of hydrophobic solvation on the alkaline hydrolysis of ethyl esters of polar substituted 2-methylpropionic acids in water

“…Table IV shows also some kinetic data and substituent parameters of 4-substituted trans-cyclohexane carbonic acid ethyl esters (22) in 50 wt% methanol-water mixtures (e = 56.5), 4-substituted bicyclooctane carbonic acid ethyl esters (z3) in 87.3 wt% ethanol-water mixtures (e = 29.6), and 13 substituted acrylic acid ethyl esters (24) in 70.0 wt% ethanol-water mixtures (e = 19.1).…”

The Preparation of 1-Carboxy-4-substituted Bicyclo[2.2.2]octanes

“…The half-ester 14 was also converted to the amino acid 21 by the known sequence.4 Alkaline permanganate oxidation14 of 10 provided 1 -carboxy-4-nitrobicyclo[2.2.2[octane (22). 15 The low yield step in this conversion is the Hoffman rearrangement of the amide 19 to the urethan 20. In preliminary work yields of the urethan were 30% or less as reported,4•11 with some starting material recovered and the bulk of the material converted to the diacid (12).…”

“…Soc., 78, 4003 (1956). (15) The preparation of 22 from 14 was carried out by Miss N. Santo, (16) J. Colonge and H. Viullemet, Bull. soc.…”

“…Ethyl bicyclo[2.2.2]octane-1,4-diearboxyIate (13) was prepared by acid-catalyzed esterification of 12. Ethyl hydrogen bicyclo-[2.2.2]octane-1,4-dicarboxylate ( 14) was prepared from 13 by the method of Roberts, et alA Compound• 14 was converted to 1bromo-4-carboxybicyclo[2.2.2]octane (15) by the method of Baker, et alu This substance was hydrolyzed by Roberts' method4 to l-bromo-4-carboxybicyclo [2.2.2] octane ( 16). 1-Hydroxy-4-carboxybicyclo[2.2.2] octane (17) was prepared from 16 by Roberts' approach.4 These known compounds exhibited physical properties in good agreement with the literature.4''28 l-Methoxy-4-carboxybicyclo[2.2,2]octane (18).-Hydroxy acid 17 (1.5 g., 0.00882 mole) and sodium hydride (2.5 g., 53% dispersion in mineral oil) were refluxed in monoglyme (50 ml.)…”