The synthesis of 2:4:6-trimethoxyphenyl-3:4-dimethoxystyryl ketone : [a methyl derivative of eriodictyol, homoeriodictyol, and hesperitin] / by Frank Tutin and Frederic W. Caton.

  • Tutin, Frank.
Date:
1910
Catalogue details

Licence: Attribution 4.0 International (CC BY 4.0)

Credit: The synthesis of 2:4:6-trimethoxyphenyl-3:4-dimethoxystyryl ketone : [a methyl derivative of eriodictyol, homoeriodictyol, and hesperitin] / by Frank Tutin and Frederic W. Caton. 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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    OH Meo<^ ^ch:ch-co-o HO Hesperitin (Tiemann and Will). _/ OH The above conclusions have now all been confirmed, inasmuch as, in the preceding paper, it is shown that eriodictyol, homo- eriodictyol, and hesperitin each yield the same product when fully methylated. Final and conclusive proof of the structure of these compounds was, however, desirable, and it appeared that this could best be obtained by the synthesis of the fully methylated product. If the views previously expressed regarding the constitution of eriodictyol, homoeriodictyol, and hesperitin be correct (Power and Tutin, Trans, loc. cit.), then these substances are 2:4: 6-triliydroxy- phenyl 3: 4-dihydroxystyryl ketone, 2:4; 6-trihydrox3'phenyl 4-hydroxyl-3-methoxystyryl ketone, and 2:4: 6-trihydroxyphenyI 3-hydroxy-4-methoxystj’ryl ketone respectively. It was therefore sought to synthesise 2:4: 6-trimethoxyphenyl 3: 4-dimethoxystyryl ketone in order that it might be compared with the compound obtained on full}’ methylating the naturally occurring substances under consideration. This has been accomplished, and the syn- thetical compound has been found to be in all respects identical with the product obtained from the three substances occurring in nature, thus affording conclusive proof of the constitution of the latter compounds. 2:4: 6-Trimethoxyacetophenone was prepared by the interaction of acetyl chloride and phloroglucinol trimethyl ether in the presence of anhydrous ferric chloride, and this ketone was condensed with vanillin methyl ether by means of “ molecular ” sodium in a manner similar to that employed by Perkin and Weizmanu (Trans., 1906, 89, 1649), when 2:4: Q-lrimethoxyphenyl 3; ^-dimethoxystijnjl ketone resulted in good yield : MeO MeO. MeO CHO -f- CH,’CO/ ^OMo MeO _ MeO MeO<^ ^ch:ch-co MeO~ MeO 0Me-tH,0. This substance gave, on heating with aluminium chloride, a hydroxytetramethoxy-compound, which melted at practically the same temperature as 2-hydroxy-4: 6-dimetho.xyphenyl 3: 4-di- methoxystyryl ketone described by Ivostanccki (Bcr., 1904, 37, 793).
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