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21st August 2013 @ 15:18

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Reaction information

*#Reaction file
reactionscheme_52 .cdx
*Reaction file type CDX
*Procedure Following a procedure reported by Whistler, the bis-tosylate, trans,trans-bi(cyclohexane)-4,4’-diylbis(methylene)bis(4-methylbenzene-sulfonate) (279 mg, 0.52 mmol) was dissolved in 6 mL of acetone. Potassium thiolacetate (154 mg, 1.35 mmol, 2.60 eq.) was added, and the suspension was heated to reflux temperature (70 °C) and stirred overnight. The resulting orange suspension was let cooling to r.t. and filtered; the white residue (TosK) was washed with Et2O (25 mL); the joined organic phases were washed with brine twice (25 mL) and dried over MgSO4. Evaporation of the solvent yielded the crude title compound (yellow solid, 161 mg, 0.47 mmol, yield 90%) that showed satisfactory purity by TLC (Rf 0.62 in 2/1 Et2O/hexane, UV 254 nm), GC (SD_FASTD, retention time 7.75 min) and NMR  analysis. This was dissolved in a small volume of DCM, treated with decolourizing charcoal and filtered; after evaporation a light yellow colour still persisted.  Part of the material (74 mg) was recrys-tallized from hot EtOH (5 mL) yielding the pure title compound (white needles, 45 mg, rcr yield 60%). 
*Yield (%) 60 %
*Type of Yield Recrystalisation
Reference(s)

PhD Thesis - 16Sep2010_final p26.pdf
 
PhD Thesis - 16Sep2010_final p138.pdf

Whistler, R. L.; Campbell, C. S. J. Org. Chem. 1966, 31, 816-818

Further information Compound 52: trans,trans-S,S’-bi(cyclohexane)-4,4’-diylbis(methylene)diethanethioate

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 51: Bistosylation of trans,trans-bi(cyclohexane)-4,4’-diyldimethanol: trans,trans-bi(cyclohexane)-4,4’-diylbis(methylene)bis(4-methylbenzene-sulfonate)
For step in multistep reaction - link to following reaction step  
Attached Files
PhD Thesis - 16Sep2010_final p138.pdf
reactionscheme_52 .cdx