The constituents of the essential oil of nutmeg / by Frederick B. Power and Arthur H. Salway.

  • Power, Frederick B. (Frederick Belding), 1853-1927.
Date:
[1907]
Catalogue details

Licence: In copyright

Credit: The constituents of the essential oil of nutmeg / by Frederick B. Power and Arthur H. Salway. 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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    quantity of an oily liquid was obtained. One part of this oil, in alcoholic solution, was heated for some time on a water-bath with hydroxylamine hydrochloride (1 part) and sodium hydroxide (1‘5 parts), after which water was added and the mixture carefully neutralised with sulphuric acid. As no solid oxime separated, the mixture was extracted with ether, the ethereal solution being washed, dried, and the solvent removed, when a brown oil was obtained which solidified on stirring with light petroleum. This solid substance was collected on a filter and crystallised from hot alcohol, from which, on cooling, it separated in small, rectangular prisms melting at 140°. The yield of this compound was about 3 grams : 0-1368 gave 0 2804 C02 and 0-1187 H20. C = 55-9 j H = 96. 0-1534 „ 0-3137 C02 „ 0-1272 H20. C = 55-8 j H = 9-2. 0T998 ,, 27-4 c.c. moist nitrogen at 16-5°and 762 mm. N=16T. C8H1(j02lN2 requires C = 55 8 ; H = 9 -3 ; N = 16'3 per cent. From these results, it appears highly probable that this compound is the dioxime of a diketone, Csli1402. The only known compound of the formula CsH1602N2 with which it might be identical is the dioxime of ethyl butyl diketone, ch3-ch2*c(:noh)-c(:noh)-ch2-ch2'CH2-ch3 (m. p. 139—141°), which has been described by Fileti and Ponzio (J. pr. Chem., 1898, [iij, 58, 364). These authors also prepared an osazone, which was found to melt at 96 — 97°. With the object of ascertaining whether our dioxime is identical with that prepared by Fileti and Ponzio, 50 grams of the fraction (b. p. 205—215°) were oxidised as previously described, and the portion of the oxidation product which was volatile in steam treated with an excess of phenylhydraziue in alcoholic solution. No -solid osazone could, however, be obtained from the product of the reaction. An attempt was also made to obtain a semicarbazone of the diketone, C8H1402, from the volatile oxidation product of the fraction 205—215°, but without success. These results therefore do not permit of any conclusion respecting the identity of the compound CsHA602N.„ here described, with the dioxime of ethyl butyl diketone prepared by Fileti and Ponzio (loc. cit.). The dioxime, C8IT1(J02N2, is a colourless, odourless substauce, sparingly soluble in cold, but readily in hot, alcohol. It is also soluble in warm ethyl acetate, from which it crystallises in fine needles, but is only sparingly soluble in benzene, and insoluble in light petroleum and in water. When warmed with dilute sulphuric acid, it first dissolved, developing a fragrant odour, but, as resinification ensued, it was impossible by this means to regenerate the ketone from which it had been formed,