By Michael Heidelberger
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Additional info for An Advanced Laboratory Manual of Organic Chemistry
In case any gummy material is formed in spite of all precautions, it may be removed, dissolved in dilute hydrochloric acid, and the above process repeated, adding the alkaline solution to the mam portion. Bone black is next added to collect a trace of gelatinous material, and the solution is filtered through large folded filters, for if the manipulations have been properly carried out the alkalinity of the solution should not be so great as to attack the paper. Since alkaline phenolic solutions are subject to oxidation, this part of the preparation should be carried out as rapidly as possible.
Addition of sodium hydroxide is then continued rapidly with vigorous stirring until the copious precipitate of the base just redissolves m the excess of alkali, solution taking place, of course, by virtue of the phenolic group exposed by the demethylation. In this way the separation of the dihydrocupreine as a gum may be avoided, as this dissolves in excess alkali only with the greatest difficulty. In case any gummy material is formed in spite of all precautions, it may be removed, dissolved in dilute hydrochloric acid, and the above process repeated, adding the alkaline solution to the mam portion.
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". The mixture is boiled 5 minutes, making certain that the reaction remains alkaline, and is filtered hot through a large Buchner funnel which, with the suction flask, has previously been warmed to prevent cracking.
An Advanced Laboratory Manual of Organic Chemistry by Michael Heidelberger