Chloropropyl p-Toluenesulfonate

A mixture of 210 g. (1.1 moles) of p-toluenesulfonyl chloride and 189 g. (2.0 moles) of trimethylene chlorohydrin [Org. Syntheses Coll. Vol. 1, 533 (1941)] is stirred and cooled to 8°. To this is added with stirring 320 ml. of 5 N sodium hydroxide solution at such a rate the temperature of the reaction mixture is held in the range 8-15°. Stirring is continued for 1 hour after the alkali has been added. A second portion of 210 g. (1.1 moles) of p-toluenesulfonyl chloride is added, followed by 320 ml. of 5 N sodium hydroxide solution in the same manner as before. The mixture is stirred for 3 hours longer, and the product is removed by extraction with ether. The ethereal extracts are washed with water and once with 20% sodium hydroxide solution, and then are dried over potassium carbonate. Distillation gives 248-275 g. (50-55%) of y-chloropropyl p-toluenesulfonate boiling at 188-192°/5 mm. 

A mixture of 54 g. (0.34 mole) of 1-methylquinolone (p. 205), 100 g. of phosphorus pentachloride, and 50 g. of phosphorus oxychloride is heated in an oil bath at 175° for 9 hours. The mixture is then distilled until the phosphorus oxychloride has passed over and the phosphorus pentachloride begins to sublime. Water is carefully added to 

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See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ ]

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