By Michael Heidelberger
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Additional info for An Advanced Laboratory Manual of Organic Chemistry
And solidifying in the receiver to a crystalline mass which melts at 38-41 °. Owing to its sensitiveness to the oxygen of the air the base is best preserved in vacuum ampoules (which may be made of thick-walled test tubes), or in glass-stoppered bottles. B. Reduction with Ferrous Sulfate and Ammonia. OCH 2 CO a H A p-Aminophenoxyacetic Acid, NHa nitroepxhceesnsooxfyadiceluticte aam cidm(p. 33a)ndarethdisssool2lvu0etidong. 5uepart s o f wat e r. bs and Heidelberger, 7. Am. Chetn. Soc. 7 ing the addition of ammonia until the solution remains definitely alkaline to litmus after shaking and boiling".
Soc, 39, 3202 (1917). 38 ADVANCED LABORATORY MANUAL markable rearrangement, somewhat analogous to that taking place when the alkyl anilines (in the form of salts) are heated to high temperatures, and consisting in the wandering of the allyl group to the o-position in the nucleus. While this reaction takes place comparatively readily in the case of the alkyl aniline salts, the alkyl phenol ethers exhibit no such phenomenon. Apparently the allyl group is the only one possessing such lability in the phenol series.
During the reduction, which requires several hours and proceeds according to the equation: OH Q#0CH< + 4Na + 4H2O > CN OH C 0 H a CH< + 4NaOH, CH 2 NH 2 the reaction is kept just acid to litmus by slowly dripping in first 50 per cent acetic acid, then the glacial acid, regulating the speed of addition by careful tests with litmus paper, as the reaction should neither be allowed to remain alkaline nor become strongly acid. When all of the sodium has been used up the solution is poured from the mercury and concentrated to about one-half volume.