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30th August 2013 @ 13:54

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Reaction information

*#Reaction file
*Reaction file type CDX 

To a solution of propane-1,3-diol (100 mmol, 7.61 g) and pyridine (95 mmol, 7.52 g) in chloroform (100 mL) at 0 °C was added para-toluene sulfonyl chloride (79 mmol, 15.06 g). The reaction was stirred for 3 h, when H20 (10 mL) and Et2O (30 mL) were added. The layers were separated and the aqueous extracted with ether. The combined organic phases were washed with 2 M HCl (20 mL), NaHCO3 solution (20 mL) and brine (20 mL), dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (SiO2, 70% ether in petrol) providing the title compound as a viscous, colourless oil (9.524 g, 51%). 

*Yield (%) 51
*Type of Yield Isolated Product Yield 
Further information Compound 204: 3-Hydroxy-propane-1-(paratoluenesulfonate)

For multistep reactions (or their steps):

Overall reaction? False 
For overall reaction - links to child reaction steps N/A 
For step in multistep reaction - link to previous reaction step N/A 
For step in multistep reaction - link to following reaction step Reaction 205
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