Preparation of tert-Butylacetic Acid and its Derivatives

Abstract

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).

About 1‐triphenylmethyl‐3‐tert‐butylaziridinone and some of its reactions

“…Commercially available (Lancaster) tert-butylacetyl chloride (1) was converted to the known [6] 2-bromo-3,3-dimethylbutanoyl chloride (2), bp 72 °C/19 mm, in near quantitative yield. The identity of 2 was confirmed by NMR.…”

“…A near-quantitative yield of the product was obtained by distilling the crude product at reduced pressure; bp 72 °C/19 mm (lit. [6] bp 93-97 °C/37 mm). 1 H-NMR (CDCl 3 ): δ 1.2 (s, 9H, tert-butyl), 4.5 (s, 1H, CH).…”

The biotransformation of t -butylacetonitrile and its boron-containing analogue trimethylamine-cyanoborane by Brevibacterium R312

“…13 C NMR: solvent (CDCl 3 ), internal standard (TMS), frequency (67.8 MHz), (CH 3 ) 3 C (28.93 ppm), (CH 3 ) 3 C (30.62 ppm), (CH 2 )CN (32.14 ppm), (CH 2 )CN (118.48 ppm). Melting point: found, 33°C; published, 32.5°C (Homeyer et al 1933) Elemental analysis: Mol. wt.…”

Synthèses stéréosélectives de deux trioxydes C18H30O3 stéréo‐isomères, d'ambréinolide et de sclaréol‐lactone à partir de dérivés du (+)‐manool

“…Le cas rCcemment mis en lumihe des terphyl-cyclohexanols B odeur de santal [6] illustre bien l'importance de ce phCnomCne, dont nous ddcrivons un nouvel exemple frappant dam le prCsent travail. (14), ambrkinolide (17). -Nous avons pr6parC ces trois substances en partant de l'acide 6a, lui-mCme obtenu en oxydant le (+)-man001 (1) suivant la mCthode lkghement modifiCe de RUZICKA et al [7].…”