Synthetic Tannins by Georg Grasser
page 38 of 193 (19%)
page 38 of 193 (19%)
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The chlorides of these compounds are obtained when phosphorus pentachloride is allowed to act upon the acids, and are as a rule crystalline. For the purpose of synthesis they may be employed as follows: 1. They readily form esters with alcohols, which on subsequent saponification with alkali are converted into the esters of the free hydroxybenzoic acids. 2. The chlorides interact energetically with esters of amino-acids, and may be coupled with amino-acids in aqueous alkaline solution. On subsequently removing the carbo-methoxy group derivatives of hydroxybenzoic acids are obtained, _e.g._, CH_3.CO_2.O.C_6H_4.CO.Cl + 2NH_2CH_2.CO.C_2H_5 = NH_2.CH_2.CO_2.C_2H_5 + HCl + CH_3.CO_2.O.C_6H_4 CO.NH.CH_2CO_2C_2H_5. CH_3.CO_2.O.C_6H_4.CO.NH.CH_2.CO_2.C_2H_5 + 3NaOH = Na_2CO_3 + C_2H_5OH + CH_3OH + HO.C_6H_4.CO.NH.CH_2.COONa. 3. In the presence of AlCl_3 the chlorides easily combine with benzene, and on removing the carbomethoxy group unsymmetrical hydroxy derivatives of benzophenone are formed:-- CH_3.CO_2.O.C_6H_4.CO.Cl + C_6H_6 = CH_3.CO_2.O.C_6H_4.CO.C_6H_5 + HCl CH_3.CO_2.O.C_6H_4.CO.C_6H_5 + 3NaOH = NaO.C_6H_4.CO.C_6H_5 + Na_3CO_3 + CH_3OH + H_2O 4. The chlorides may be coupled with free hydroxybenzoic acids, and on removing the carbomethoxy group didepsides are obtained. Repetition of |
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