The reduction from ketone to alcohol and the subsequent operations were carried out as previously described. The oil, remaining after treatment with ether to remove unchanged ketoamine, could not be crystallized. An oxalate was obtained, however, by dissolving the oil in absolute alcohol and adding an alcoholic solution of oxalic acid. The resulting precipitate was recrystallized from alcohol; m. p. 185-186°(dec.).Anal. Caled, for C2iH36OioN2: C, 56.3; , 7.0. Found: C, 56.2; H, 7.1.N-Benzoyl Derivative.-This derivative was prepared by the ijchotten-Baumann reaction and was recrystallized from alcohol and water; m. p. 113°.
222-2230 with darkening. When samples of this material and the original were mixed there was no change in the melting behavior.The yellow product dissolved in alcohol with subsequent separation of colorless crystals. When dry hydrogen chloride was passed into this suspension the crystals first dissolved with subsequent separation of the yellow solid. When suspended in water or ether, the yellow substance did not dissolve but lost color immediately to give the same colorless crystals. The yellow substance itself seemed quite stable, suffering no apparent loss in color on standing for a week.A quantity of the yellow substance was treated with alcohol, and the resulting colorless crystals filtered off, washed with alcohol until free from chloride, and recrystallized from alcohol; in. p. 225-227°with darkening. This was assumed to be the same substance as the dehydrated N-(3,4-dihydroxyphenacyl) N-(d-hydroxyethyl)benzamide, with the melting point raised by better puri-fication. The analysis indicated the loss of one molecule of water during the treatment with alcoholic hydrogen chloride.The colorless product gave an emerald green color with ferric chloride solution. It was insoluble in 5% sodium carbonate solution.
The proper scope and content of an introductory course in organic chemistry for universities, the course being offered to students of other subjects for professional use (doctors, engineers, etc.), as well as to students of chemistry proper, are discussed. Therefrom follows an indication of the changes already effected, or to be effected, in the methods and scope of the teaching of the course in Columbia University, New York City. Directions for the preparation of caffeine from tea are included.
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