Domestic coal tar light oil sources provide annually a total of 10 to 15 million gallons of mixed xylenes and C» aromatics, in the form of 1°, 3°, 5°, 10°, and industrial pure xylenes, together with solvent naphthas
Purified and dried acetylene was bubbled through 50 cc. of dry ether in a flask with a mercury-sealed stirrer for one-half hour. Solutions of 1 g. of potassium in 15 cc. of dry tertiary amyl alcohol, and of 1 g. of dehydroandrosterone in 50 cc. of dry ether and 5 cc. of dry benzene were added dropwise during one-half hour, and stirring continued for five hours longer, acetylene being bubbled through the reaction mixture during the whole period and the reaction flask being maintained at room temperature. The reaction mixture was then acidified with saturated ammonium chloride solution containing a little hydrochloric acid and thoroughly extracted with ether. The ether was washed, dried over sodium sulfate, and evaporated under reduced pressure. The last traces of alcohol were removed in a stream of carbon dioxide. The residue was crystallized twice from methanol or aqueous methanol; yield 80-85%; m. p. 240-242°, [ ]25 -119°( chloroform).Besides avoiding the use of liquid ammonia, this method has several other advantages over the methods of Ruzicka and Hofmann1 and Kathol, et alA The reaction time is less, and the use of Girard's ketone reagent for removing dehydroandrosterone is unnecessary.
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