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21st August 2013 @ 13:53

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Reaction information

*#Reaction file
reactionscheme_50.cdx
*Reaction file type CDX
*Procedure Following a standard procedure, a 50 mL Schlenk flask was loaded with the acid trans,trans-Bi(cyclohexane)-4,4’-dicarboxylic acid (50 mg, 0.20 mmol), then evacuated and refilled with argon before adding distilled THF (10 mL). A condenser was fitted onto the flask and LiAlH4 (60 mg, 1.58 mmol, 7.90 eq.) was added at once. The reaction was heated to 60° C for 1.5 h; after cooling the excess hydride was quenched with HCl 2 N (2 mL, dropwise). The suspension was diluted with Et2O (20 mL) and washed with water (3 x 20 mL); this was extracted with Et2O (2 x 15 mL) and the organic fractions were joined and dried over MgSO4. Evaporation of the solvent yielded the crude product (49 mg) that was column chromatographed over silica gel, using EtOAc as eluent (Rf 0.5), to obtain the title compound (29 mg, 0.13 mmol, yield 64%). This was analyzed by NMR and found to contain about 10% cis- contaminant, yet it was used in the next step without further purification.
*Yield (%) 64 %
*Type of Yield Reaction yield
Reference(s)
PhD Thesis - 16Sep2010_final p26.pdf
 
PhD Thesis - 16Sep2010_final p136-137.pdf
Further information Compound 50: trans,trans-bi(cyclohexane)-4,4’-diyldimethanol

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 49: Hydrolysis of dimethylbi(cyclohexane)-4,4’-dicarboxylate: trans,trans-bi(cyclohexane)-4,4’-dicarboxylic acid
For step in multistep reaction - link to following reaction step Reaction 51: Bistosylation of trans,trans-bi(cyclohexane)-4,4’-diyldimethanol: trans,trans-bi(cyclohexane)-4,4’-diylbis(methylene)bis(4-methylbenzene-sulfonate)
Attached Files
reactionscheme_50.cdx
PhD Thesis - 16Sep2010_final p136-137.pdf