The reactions between phenyl chloroform and the sodio derivatives of ethyl malonate. Subsidiary thesis: The constitution of the natural gases of New Zealand (1929)
When chloroform is condensed with 2 mols. of ethyl disodio-malonate in alcoholic solution ethyl sodio-dicarbethoxy-glutacomate (I) is formed. (Conrad and Guthzeit, Ann. 222 256.) [diagram here]. Under the proper conditions a yield of 50% is obtained. (Thele and Thorpe, J.C.S. 99. 2187) This on Hydrolysis and boiling with hydrochloric acid yields glutaconic acid. (II) The product I may also be methylated with methyl iodide when, on treatment with concentrated sodium ethyl sodio-x-methyl-carbethoxy-glutaconate (III) is obtained which on hydrolysis and boiling with hydrochloric acid similarly yields –methyl-glutaconic acid (IV) [diagram here]. The present investigation was undertaken to ascertain whether phenyl ethloroform (bonzotrichloride) behaved similarly to chloroform, and yielded the – Phenyl substituted analogues of I, II, III, and IV. and if not, to find what course the reaction followed, and study the products found. The β -phenyl-&-methyl-β –phenyl-glutasonic acids, phenyl analogues of II and IV above, have been prepared by Thorpe (J.C.S. 1912. 101 868) by condensing ethylphenyl-propiolate and ethyl sodio malonate and characterised and its properties investigated by Thorpe and Wood. (J.C.S. 103 P.F. 1569-1578).
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Lorimer, A. E. (University of Canterbury. Chemistry, 1930)Ethyl malonate belongs to the class of tautomeric compounds which exist in more than one structural form in equilibrium with one another. Ethyl malonate consists almost wholly of the ketonic form I. [Diagram] and ...
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