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49), allowing the water boiling off to escape until the temperature has again reached that of the constant-boiling hydrate, when an air-condenser is attached and the boiling continued for four hours The methyl bromide liberated may be collected if desired by leading tubes from the air-condenser into a test tube immersed in a freezing mixture. Phenolic ethers, of which dihydroquinine is an example, may be dealkylated by heating with acids Hydrochloric aad is often used, but the reaction rarely takes place at the boiling point of the constant-boiling hydrate and is therefore generally carried out in sealed tubes The pressure developed by the methyl chloride liberated often results in the breakage of tubes, but can be avoided to some extent by frequently opening and resealmg the tubes Concentrated hydriodic aad is also a useful dealkylating agent, but is relatively expensive, and hydrobromic aad may therefore be used to advantage in many cases especially when large amounts of material are m question.

As the base is readily oxidized by the air * Jacobs and Hddelberger, /. Biol. Chem. 21, 113 (1915). 46 ADVANCED LABORATORY MANUAL the acid solution is covered by a layer of ether, ice is added, and the compound only then liberated by making very strongly alkaline with 50 per cent sodium hydroxide, being sure that enough ice is present to keep the mixture cold. After shaking cautiously the ether is removed and the alkaline solution again shaken out several times with ether. The combined ethereal extracts are dried over sodium sulfate and sodium hydroxide and concentrated, and the residue is distilled in vacuo.

Taylor of the Rockefeller Institute for Medical Research for placing at his disposal the results of working over the method of Fischer and Dilthey, Ann. 335, 338 (1904)- OF ORGANIC CHEMISTRY 65 slowly through a dropping funnel 1 equivalent of the ethyl iodide. The mixture is finally boiled, and when neutral to moistened red litmus the second half of the sodium is dissolved in the remainder of the alcohol, the neutral reaction mixture added, and the balance of the ethyl iodide slowly dripped in, after which the mixture is boiled over night, when it should again be neutral.

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An Advanced Laboratory Manual of Organic Chemistry by Michael Heidelberger

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