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Encyclopedia Britannica - Main :: GUI-HAN |
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H2C CHCH2 H2CCHCH2 H2CCHCH2CO2H H2CCHCH2 NMe CHOH NN/1e CO NI N Me NMe CIH I ~I II HZCCHCHI 2 HZCCHI CHI 2 HZCCI HCOZH HZ CHCH Tropine
synthesis of tropine
Tropic acid, C9H1003, the other decomposition product of atropine, is a saturated hydroxy-acid which is readily converted into atropic acid, C9H802, by dehydrating agents. This latter acid is shown by all its reactions to be C6H5C(:CH2)CO2H, a fact which is confirmed by its synthesis from acetophenone
phosphorus pentachloride, followed by the decomposition of the resulting chloride with an alcoholic solution of potassium cyanide
hydrolysis of the nitrile so formed. These results show that tropic acid must be either C6H5CH(CH2OH)CO2H or C6II5C(OH)(CH3)CO2H, and since the latter compound has been prepared from acetophenone
hydrolysis and is an isomer of tropic acid, it follows that tropic acid must be represented by the former of the two formulae. Hence the alkaloid atropine, being a tropine-tropate, must have the annexed formula
H2CCHCH2 CH2OH NMe CI HOCOCH I 1 H2CCI H--CH2 C6H5
Atropine. End of Article: H2C If you wish, you can link directly to this article.
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