Some derivatives of oleanol / by Frank Tutin and William J.S. Naunton.

  • Tutin, Frank.
Date:
[1913?]
Catalogue details

Licence: Public Domain Mark

Credit: Some derivatives of oleanol / by Frank Tutin and William J.S. Naunton. Source: Wellcome Collection.

    7/16 (page 2054)
    identified by its general properties and boiling point as acetic anhydride. The solid residue in the distillation flask was dissolved in a small amount of hot petroleum (b. p. 90—120°), and boiling ethyl acetate added. A substance then separated in small, colour¬ less, flattened prisms, which melted at 315—316°: 0-0995* gave 0‘2860 C02 and 0-0892 H20. 0=78-4; H = 100. C66H102O7 requires C = 78-7; H = 10-l per cent. It is thus evident that the change undergone by diacetyloleanol on heating is analogous to that suffered by diacetylprunol (Power and Moore, loc. cit.), and proceeds according to the following equation: 2C35pIwO5 = C66H102O7+ (CH3*C0)20. Oxidation of Oleanol with Potassium Permanganate. Formation of Oleanone, C29H4604. A quantity (10 grams) of oleanol was dissolved in glacial acetic acid, and a solution of 7 grams of potassium permanganate in a large volume of 95 per cent, acetic acid then gradually added. After keeping the mixture for an hour it was decolorised by means of sulphur dioxide, when, on pouring the solution into water, a quantity of solid was precipitated. The latter was isolated by means of ether, and the ethereal solution shaken with aqueous alkalis. This treatment, however, removed only acetic acid and relatively small amounts of amorphous products. The ethereal solution was then evaporated, and the residue crystallised from ethyl acetate. This was achieved only with considerable difficulty, owing to the great tendency of the product to separate in a colloidal condition. The material which had been once crystallised from ethyl acetate was then recrystallised several times from methyl alcohol, when it appeared to be dimorphous. It formed either glistening, colourless needles, or elongated, lustrous plates, both forms melting at 304°. The yield was about 40 per cent, of the weight of the oleanol employed: 0 1299 gave 0-3625 C02 and 0-1170 H20. C = 76‘l; H = 10-0. 0-1331 „ 0-3712 C02 „ 0T202 H20. C = 76'0; 11 = 10-0. C29H4604 requires C = 760; 11 = 10*0 per cent. It appears, therefore, that on oxidation oleanol suffers the loss of the elements C2H4 and the addition of one atom of oxygen. It is highly probable that the resulting product, C29H4604, is a ketone, although no oxime could be prepared from it, and it is proposed to designate it oleanone. Oleanone is moderately soluble in most organic solvents, and a * Dried at 130°.