Preparation and Properties of tert-BuTYLACETic Acid 4209 solution was filtered and treated with dry acetylene under a pressure of 10 cm. of mercury.10 The precipitate of acetylide was collected on a fluted filter and after washing three times with 10 ml. of alcohol crystallized twice from «-propanol. The filtrate from the reaction mixture on standing lost acetylene and, due to the decomposition of the monoalkylmercuri acetylide, deposited more of the bis compound.Analysis of Compounds.-Decyl mercury bromide was analyzed according to the method of White.11 Caled, for CioHuHgBr: Hg, 47.56. Found: Hg, 47.40. The acetylides were decomposed by White's process11 and the mercury determined by the volumetric procedure of Rupp.12 Results are listed in Table I. Summary 1. Decyl mercury bromide and four new bisalkylmercury acetylides have been prepared and their melting points reported.2. «-Propanol has been found to be a suitable medium from which to crystallize members of the bisalkylmercury acetylide series.3. The melting point curves of the dialkynyl mercurys and the bisalkylmercury acetylides are very similar and lie approximately 29°a part.4. The values for the melting points of the alkyl mercury bromides as high as the decyl member have been determined on pure samples. The melting point curve shows a small but regular alternation. 5. A simplified procedure for the preparation of straight chain alcohols has been reported.(10) Vaughn, ibid., 9, 52S (1932).
Compared to other simple organic esters, the alkyl carbonates have found little application in synthetic reactions. This is the first of several papers reporting investigations which greatly extend the uses of this interesting class of compounds. Scattered through the literature may be found a few instances in which alkyl carbonates have been employed but none of these suggests a type reaction of broad applicability or utility.The present paper describes a method of condensing alkyl carbonates with organic esters to produce malonic esters. The new synthesis of
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