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21st August 2013 @ 14:20

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Reaction information

*#Reaction file
reactionscheme_51.cdx
*Reaction file type CDX
*Procedure Following a procedure reported by Swepston, a 25 mL Schlenk flask containing compound trans,trans-Bi(cyclohexane)-4,4’-diyldimethanol (212 mg, 0.94 mmol) was evacuated and refilled with argon before adding pyridine (2 mL). The resulting suspension was stirred at r.t. for 10 minutes; after cooling to 0 °C p-toluenesulfonylchloride (448 mg, 2.35 mmol, 2.50 eq.) was added, under argon, and the reaction mixture was kept in the fridge (1 °C) overnight.  After warming to r.t. the mixture was diluted with water (5 mL) and filtered; the solid was washed with water and then dissolved using a mixture of MeOH/DCM. Evaporation of the solvent yielded the crude product (white solid, 473 mg) that was column chromatographed using DCM as eluent (Rf 0.35). NMR analysis on the purified compound (417 mg) showed about 10% of cis- signal. Recrystallization from boiling EtOH (45 mL) yielded the title compound with 97% purity, as estimated by 1H NMR (white needles, 279 mg, 0.52 mmol, yield 55%).
*Yield (%) 55 %
*Type of Yield Isolated pure product
Reference(s)

PhD Thesis - 16Sep2010_final p26.pdf
 
PhD Thesis - 16Sep2010_final p137-138.pdf

Swepston, P. N.; Lin, S.-T.; Hawkins, A.; Humphrey, S.; Siegel, S.; Cordes, A. W. J. Org. Chem. 1981, 46, 3754-3756

Further information Compound 51: trans,trans-bi(cyclohexane)-4,4’-diylbis(methylene)bis(4-methylbenzene-sulfonate)

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 50: Reduction of trans,trans-bi(cyclohexane)-4,4’-dicarboxylic acid: trans,trans-bi(cyclohexane)-4,4’-diyldimethanol
For step in multistep reaction - link to following reaction step Reaction 52: Displacement of tosyl-group using a thioacetate: trans,trans-S,S’-bi(cyclohexane)-4,4’-diylbis(methylene)diethanethioate
Attached Files
reactionscheme_51.cdx
PhD Thesis - 16Sep2010_final p137-138.pdf