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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    was collected, and recrystallised from methyl alcohol, when it formed glistening prisms, melting at 62—64°: 0*1468 gave 0-3180 C02 and 0’0725 H20. C = 59’0; H=5 5. 0-2142 „ 0-2225 AgL OMe = 13'7.~ C10H9O4*OMe requires C = 58 9; H = 5*3; OMe=13‘8 per cent. 2 :5-Diacetoxya7iisole.—This was prepared by the action of acetic anhydride on 2:5-dihydroxyanisole, as in the preceding case. 2:5-Diacetoxyanisole crystallises from methyl alcohol in glistening, prismatic needles, melting at 93—94° : 01258 gave 0*2720 C02 and 0*0605 H20. C = 58*9; H = 5*3. CnH1205 requires C = 58*9; H = 5*3 per cent. It is therefore evident that the product of the prolonged action of boiling aqueous potassium hydroxide on scopoletin is 2:4-di- hydroxyanisole, and the formation of this compound is only possible, as already indicated, if scopoletin is 4-hydroxy-5-methoxy- coumarin. Attempts to isolate the corresponding 2:4-dihydroxy- 5-methoxybenzoic acid, which must be formed as an intermediate product, were unsuccessful. (2) Formation of 2 :4- Dihy dr oxy-b-m ethoxy cinnamic Acid. If scopoletin is dissolved in 10—20 per cent, aqueous potassium hydroxide, and the solution boiled for a few minutes, the lactone grouping is hydrolysed, and the liquid then shows no fluorescence. A quantity (10 grams) of scopoletin was added to 100 c.c. of boiling 20 per cent, aqueous potassium hydroxide, and the solution boiled for four minutes. The alkaline liquid was then at once cooled, ice added, and acidified by the addition of 40 c.c. of concen¬ trated hydrochloric acid, mixed with an equal volume of ice, the temperature being kept below 10°. After a short time, a yellow, crystalline precipitate separated, which was collected, well washed with ice-water, and dried in a desiccator. The product so obtained amounted to 9 grams. It crystallised from hot water in bright yellow needles, melting and decomposing at 178—180°: 0*5778,* on heating at 110°, lost 0*0468 H20. H20 = 8*l. 0-1426 f gave 0-2995 C02 and 0*0650 IT20. C = 57’3; H'=5-0. 0-1628 f „ 0*1780 AgL OMe=14'4/ C10H10O5,H2O requires H2O = 80 per cent. C9H704*0Me requires C = 57*l; H = 4'8; OMe = 14*7 per cent. The substance is therefore the coumaric acid corresponding with scopoletin, or 2 :k-dihydroxy-'o-methoxycinnamic acid, sodium derivatives of which were obtained by Kunz-Krause (Ber., 1898, 31, 1192).
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