Whitby group

 

This post is compatible for submission to ChemSpider Reactions. See [blog=44639]ChemSpider Reactions template - help and further information[/blog] for help when using it. Reaction information *#Reaction file [data]39206[/data]  *Reaction file type CDX  *Procedure 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  Reference(s) [data]39208[/data][data]39210[/data] 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