The constitution of umbellulone. Pt. II / by Frank Tutin.

  • Tutin, Frank.
Date:
1907
Catalogue details

Licence: In copyright

Credit: The constitution of umbellulone. Pt. II / by Frank Tutin. Source: Wellcome Collection.

Provider: This material has been provided by The Royal College of Surgeons of England. The original may be consulted at The Royal College of Surgeons of England.

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    contained in the distillate were converted into their barium salts, and, from the latter, silver salts were prepared. These gave some silver ^-S-hydroxy-a-wopropyl-n-hexoate, but the mother liquors from this yielded a salt which, after recrystallisation from water, was analysed with the following result : 0-1803 gave 0-1158 Ag. Ag = 64-2. CgHgOgAg requires Ag = 64-6 per cent. This salt was thus identified as silver acetate. The liquid remaining in the distilling flask after the first steam dis- tillation, and which contained the non-volatile products of the oxidation, was repeatedly extracted with ether, and the ethereal liquid washed* dried, and evaporated. By this means a syrupy residue was obtained which, on standing for some time, became crystalline. The solid acid thus obtained was recrystallised from benzene, after which it melted at about 117 118 . W^hen heated to 180° it evolved gas and gave a strong odour resembling that of valeric acid, from which it appeared probable that it contained a little of a substituted malonic acid. It was therefore heated at 180° until evolution of gas ceased, after which, on standing for some time, it slowly solidified. It was then again crystallised from benzene, and was obtained in tufts of needles, which melted sharply at 120°. 0-1007 ga've 0-1946 COg and 0-0699 HgO. C = 52-7 ; H=7-7. requires C = 52-5 ; H = 7-5 per cent. 0-1619 required 20-3 c.c. of iV/10 NaOH for neutralisation. C5Hjq(C02H)2 requires 20-2 c.c. This acid had the same melting point (120°) as a specimen of isopro- pylsuccinic acid obtained from Prof. Crossley, and was evidently identi- cal with it, as a mixture of the two preparations also melted at the same temperature. For the purpose of confirming the identity of the solid acid (obtained by the oxidation of Z-8-hydroxy-a-isopropyl-?i-hexoic acid) with zsopropylsuccinic acid, the remaining quantity of the former was converted into the ammonium salt, and this heated at 160° for four hours. In this way an imide was obtained which crystallised from water in plates melting at 62°, and a mixture of this substance with isopropylsuccinimide also melted at this temperature. The Wellcome Chemical Reseaech Laboratoeies, London, E.C. R. CLAY AND SONS, LTD., BREAD ST HILL, E.C., AND BUNOAY, Sl’FFOLK
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