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By Michael Heidelberger
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Extra resources for An Advanced Laboratory Manual of Organic Chemistry
The essential requirement m the preparation of diethylmalonic ester and "veronal" is that all reagents must be absolutely anhydrous, otherwise the yields will be vanishingly small. All reagents and solutions must therefore be protected from the moisture of the air after drying. Required are ioo g. of carefully dried and freshly distilled malomc ester, prepared according to the directions in the elementary text books, 28 8 g. of sodium (2 molecular equivalents), 380 cc of absolute alcohol (dried by adding to ordinary absolute alcohol enough sodium to combine with 1 per cent of water and distilling), and 195 g of carefully dried and freshly distilled ethyl iodide (2 molecular equivalents).
Under the conditions given very little addition of hydrobromic acid takes place at the double bond, although this would undoubtedly occur on long standing of the saturated solution in the cold. The mixture is then poured into water and the crude bromide separated and washed first with normal sodium 'Reverdin and Lokietek, Bull soc chim  17, 407 (1915). •Merlmg and Jacobi, Ann. 278, 11 (1894) OF ORGANIC CHEMISTRY 37 hydroxide solution and then with water. After drying over calcium chloride and distilling, the yield should be 85 per cent of the theory, boiling at 70-1 °.
3. o-Allylphenol (o-Chavicol). OH CH a CH:CH 9 . 8 Allyl phenyl ether is boiled under an air condenser until the temperature no longer rises, a process requiring four to six hours. From an initial temperature of about 1900 the thermometer finally rises to about 220 0 . The gradual increase m boiling point is due to a reT Claisen and Eisleb, Ann 401, 21 (1913); 418, 78 (1918). 'Claisen, loc. cit; Jacobs and Heidelberger, /. Am Ckem. 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.
An Advanced Laboratory Manual of Organic Chemistry by Michael Heidelberger