[BH4-].[Na+].[CH2:3]([C:8]([C:10]1[CH:15]=[CH:14][C:13]([SH:16])=[CH:12][CH:11]=1)=O)[C:4]([CH3:7])([CH3:6])[CH3:5].O.S(=O)(=O)(O)O>COCCOCCOC>[CH2:8]([C:10]1[CH:11]=[CH:12][C:13]([SH:16])=[CH:14][CH:15]=1)[CH2:3][C:4]([CH3:7])([CH3:6])[CH3:5]7.5 g (0.2 mol) of sodium borohydride in 140 ml of diethylene glycol dimethyl ether are initially introduced, and a solution of 41.6 g (0.2 mol) of 4-(neopentylcarbonyl)-thiophenol in 60 ml of diethylene glycol dimethyl ether are added at 30°-40° C. The mixture is further reacted at 120° C. for 2 hours, 100 ml of water are added with ice-cooling, the mixture is acidified with 20% strength sulphuric acid, and another 200 ml of water are added. The reaction mixture is now extracted with 250 ml of methylenechloride, the organic phase is extracted with 250 ml of water, dried over magnesium sulphate and distilled through a split ring column to give 23 g (60% of theory) of 4-(neohexyl)-thiophenol of boiling point 98° C./0.4 mbar.
Loading…
