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By Michael Heidelberger

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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. 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.

83, 535 C1903). Ckem, Soc. 79, 380 (1901). 8 voi» P$cJimai}a, $frf 30, ^504 (1887). C:NOSO2Na R' R. CO. CO. R ' + NH 4 NaSO 4 The solution is finally diluted with water, cooled, and the crude camphorquinone filtered off and purified by distillation with steam. The yield should be about 7 g. The qumone forms yellow prisms and needles which melt at 198 0 . It sublimes rapidly above ioo°, and, like camphor itself, is quite volatile at room temperature C. Oxidation with Atmospheric Oxygen: Camphoric Acid.

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. 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.

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