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21st August 2013 @ 12:25

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Reaction information

*#Reaction file
reactionscheme_49 .cdx
*Reaction file type CDX
*Procedure As reported by Cannon, the ester, dimethylbi(cyclohexane)-4,4’-dicarboxylate (1.61 g, 5.70 mmol) was hydrolized by refluxing for 4 h in presence of NaOH (0.72 g, 18.0 mmol, 3.16 eq.), in a mixture of EtOH (13 mL) and water (3.5 mL) at 75° C. After cooling, most of the EtOH was vacuum evaporated; water was added (25 mL), followed by concentrated HCl (7 mL) which caused the precipitation of the title compound. This was filtered, washed with water and dried, initially in air and then in high vacuum (at least 10 h to ensure dryness), yielding the mixture of acid diastereomers (white solid, 1.29 g, 5.07 mmol, hydrolysis yield 89%) . The solid was ground and tightly packed in a small reaction tube; this was placed in a sand bath inside an aluminium block preheated to 275° C. After 3 h the material was left cooling then dissolved by sonication in Na2CO3 (sat.); after adding of decolourizing coal the suspension was filtered. Addition of HCl (10% w/v, 20 mL) caused the precipitation of the title compound that was filtered, washed with water and dried in air for several days. The product (white solid, 1.01 g, 3.97 mmol, yield 70%), as analyzed by NMR, was found to be 90% single diastereomer: the assignment to the trans,trans- geometry was supported by the comparison of the Mp with that reported in literature.
*Yield (%) 70 %
*Type of Yield Isolated pure product

PhD Thesis - 16Sep2010_final p26.pdf
PhD Thesis - 16Sep2010_final p136.pdf

Cannon, J. G.; Liang, C.-Y. Synth. Comm. 1995, 25, 14, 2079-2089.

Further information Compound 49: trans,trans-bi(cyclohexane)-4,4’-dicarboxylic acid

For multistep reactions (or their steps):

Overall reaction? False
For overall reaction - links to child reaction steps  
For step in multistep reaction - link to previous reaction step Reaction 48: Hydrogenation of methyl ester biphenyl-dicarboxylate: dimethylbi(cyclohexane)-4,4’-dicarboxylate
For step in multistep reaction - link to following reaction step Reaction 50: Reduction of trans,trans-bi(cyclohexane)-4,4’-dicarboxylic acid: trans,trans-bi(cyclohexane)-4,4’-diyldimethanol
Attached Files
reactionscheme_49 .cdx
PhD Thesis - 16Sep2010_final p136.pdf
PhD Thesis - 16Sep2010_final p26.pdf