The reactions between phenyl chloroform and the sodio derivatives of ethyl malonate. Subsidiary thesis: The constitution of the natural gases of New Zealand (1929)
AuthorsGray, C. M.show all
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).