The constitution of scopoletin / by Charles W. Moore.

  • Moore, Charles W.
Date:
[1911?]
Catalogue details

Licence: In copyright

Credit: The constitution of scopoletin / by Charles W. Moore. Source: Wellcome Collection.

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    prolonged boiling with aqueous potassium hydroxide, and tho dimethyl ether of aesculetin shows a similar stability. Experimental. The scopoletin employed was obtained from the rhizome of (Selsemium sempervirens, Aiton (Trans., 1910, 97, 2223), in which it occurs to the extent of about 0'05 per cent. It forms yellow needles, melting at 204°, and in alkaline solution shows a fine blue fluorescence. Action of Potassium Hydroxide on Scopoletin. (1) Formation of 2 ‘A-Dihydroxyanisole. With the endeavour to obtain the coumaric acid corresponding with scopoletin, a quantity (4 grams) of the latter was boiled for nine hours with 50 c.c. of a 45 per cent, aqueous solution of potassium hydroxide. The resulting dark-coloured aqueous solution was acidified, and extracted with ether. The ethereal extract was dried, and the solvent removed, when a dark brown, syrupy liquid was obtained, which showed no tendency to crystallise. The product was therefore distilled under diminished pressure, when the greater part of it passed over as an almost colourless, viscid liquid, which, when dissolved in dry benzene, separated, on keeping, in glistening prisms (T5 grams), melting at 66—68°. (Found, C = 59*8; H = 5*9; OMe-22‘0. Calc., C = 60’0; H==5*7; OMe = 22*1 per cent.). The compound is therefore a dihydroxyanisole, and from its melting point must be 2:4-dihydroxyanisole, the only possible alternative being the 2:5-dihydroxy-compound, which, however, melts at 84°. For the purpose of comparison, a small quantity of the latter was prepared by the reduction of the corresponding quinone, as described by Witt (Ber., 1888, 21, 605). Methoxy- quinone was found to melt at 145°, instead of 140°, as recorded {Joe. cit.), and possesses no quinone-like odour. On reduction it yields 2:5-dihydroxyanisole, which crystallises from benzene in glistening prisms, melting at 84°, as recorded in the literature {loc. cit.). Further confirmation as to the identity of the above-described compound with 2 :4-dihydroxyanisole was obtained by preparing its diacetyl derivative, and comparing this with 2 :5-diacetoxyanisole. 2 -A-Diacetoxyanisole.—2 :4-Dihydroxyanisole was boiled for a few minutes with acetic anhydride in the presence of a trace of d-camphorsulphonic acid. The solution was then poured into water, when, after a time, a crystalline precipitate separated. This
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