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21st August 2013 @ 11:25

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Reaction information

*#Reaction file
reactionscheme_48 .cdx
*Reaction file type CDX
*Procedure Following a procedure reported by Cannon, a glass vessel was loaded with methyl ester biphenyl-dicarboxylate (2.0 g, 7.4 mmol), PtO2 (33 mg, 20 mol%), Pd/C (5% Pd, 66 mg, 0.4 mol%) and AcOH (50 mL), and the mixture was sonicated shortly. The vessel was fitted in a steel high pressure apparatus that was vented and then filled withH2 until a pressure of 350 psi was established. The reaction was heated to 50 °C and stirred for several days: addition of more gas was needed to keep the pressure at the set-point. Monitoring by GC (SD_FASTD) was carried on by letting cooling the reaction and releasing the pressure prior to sampling: after 2 d this showed 3 main peaks at 7.13, 7.29 and 7.46 min, 2 minor peaks at 7.59 and 7.74 min, and starting material as a trace at 8.56 min; after further 2 d only the three main peaks were left, and these were assigned to the three possible diastereomeric products. The mixture was filtered through filter paper (double layer), taken up in DCM (50 mL), washed with water (2 x 100 mL) and dried over MgSO4. The crude product (white solid, 1.97 g, 6.98 mmol, yield 94%) was used in the next step without further purification; the completeness of the reduction was assessed by 1H NMR from the disappearance of the aromatic signals.
*Yield (%) 94 %
*Type of Yield Crude product
Reference(s)

PhD Thesis - 16Sep2010_final p26.pdf
 
PhD Thesis - 16Sep2010_final p135.pdf

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

Further information Compound 48: dimethylbi(cyclohexane)-4,4’-dicarboxylate

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  
For step in multistep reaction - link to following reaction step Reaction 49: Hydrolysis of dimethylbi(cyclohexane)-4,4’-dicarboxylate: trans,trans-bi(cyclohexane)-4,4’-dicarboxylic acid
Attached Files
PhD Thesis - 16Sep2010_final p26.pdf
reactionscheme_48 .cdx
PhD Thesis - 16Sep2010_final p135.pdf