The synthesis of substances allied to cotarnine / by Arthur H. Salway.

  • Salway, Arthur Henry.
Date:
1909
Catalogue details

Licence: Attribution 4.0 International (CC BY 4.0)

Credit: The synthesis of substances allied to cotarnine / by 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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    Z-Methoxy-4:: h-methyle'nedioxycinnamic Acid, CH ^Oj/^CHICH-COsH OMe One hundred and fifty grams of myristicinaldehyde were dissolved in 400 grams of ethyl acetate, and to this solution 37’5 grams of sodium, finely divided by vigorous agitation with boiling toluene, were added. The violent reaction which immediately ensued was moderated by cooling the mixture. When the action had subsided, the mixture was kept at the ordinary temperature for some time, after which the product was hydrolysed by heating for half an hour with an excess of alcoholic potash. The alcohol was then removed as completely as possible, water added, and the alkaline liquid extracted with chloroform to remove resinous matter. On acidifying with dilute sulphuric acid, a grey precipitate was obtained, which was crystallised from glacial acetic acid. The yield of methoxymethylenedioxycinnamic acid was 137 grams : OT342 gave 0-2914 COg and 0-0554 HgO. C = 59-2 ; H = 4-6. CiiHioOg requires 0 = 59-5 ; H = 4-5 per cent. Z-MethoxyA : b-methylenedioxycinnamic acid is readily soluble in hot acetic acid, from which, on cooling, it crystallises in well-formed, colourless, prismatic needles, sintering at 220° and melting and decomposing at 228°. It is only moderately soluble in boiling alcohol, and is deposited from this solvent in thin, flat plates. It is practically insoluble in water and only very sparingly soluble in ether. ^-Z-McthoxyA \ 6-methylenedioxypropionic Acid, CH <;0/^CH,-CH,-CO,H ' °\/ OMe Fifty grams of 3-methoxy-4 : 5-methylenedioxycinnamic acid were dissolved in dilute sodium hydroxide, and reduced with 800 grams of sodium amalgam (4 per cent.) at the ordinary temperature. The liquid was mechanically stirred throughout the reduction, whilst the accumulation of alkali in the mixture was prevented by the periodic addition of hydrochloric acid. At the end of the reaction the alkaline liquid was acidified and the precipitated oil extracted with ether, when, on evaporating the solvent, a viscid, brown oil was obtained. This solidified after long keeping, and was then crystallised from benzene