1-Methoxy-2-propanol → Pyridine, 2,3,5-trichloro-

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Reaction Steps

To a 500 milliliter, 3-neck flask which was fitted with a reflux condenser, thermometer, stirrer and heater was added 100 milliliters of 1-methoxy-2-propanol, 25.1 grams (0.10 mole) of pentachloropyridine and 39.0 grams (0.60 gram atom) of zinc dust. The flask was heated, with stirring, to 90° C. until all the pentachloropyridine was dissolved. At this time, 100 milliliters of concentrated ammonium hydroxide was added over a 5 hour period. The pH of the mixture was ~12. The mixture was refluxed for 32 hours and the reaction mixture was diluted with two volumes of water and 100 milliliters of toluene. The mixture was filtered to remove insolubles. The toluene was removed by fractionation leaving 30.0 grams of crude 2,3,5-trichloropyridine as an amber-colored oil. Analysis by gas-liquid chromatography showed a yield of 2.1 grams of the desired product (12 percent of theoretical).

Provenance & Evidence