The Synthesis of 1, 2, 3, Triphenylpropane

Abstract

The preparation of symmetrical triphenyl-propane has been carried out by several different methods, principally by German chemists. Altho there is very little in the chemical literature on this compound, the method most frequently used was from tribromhydrin by the Friedel-Craft reaction. Cohn [1] (Paul) obtained a hydrocarbon of the composition C21 H2O which was probably symmetrical triphenyl-propane, when 10 gms. of cyclophenylenebenzylidene oxide, or 10 gms. of orthohydroxybenzhydrylamine was heated at 140-150 degrees C. with 40-50 cc. of fuming hydriodic acid and 10 gms. of red phosphorus. The liquid, after shaking with ether, was made alkaline, distilled with steam, and after shaking with ether again, the ethereal solution was evaporated. A thick, heavy oil was obtained. Claus and Mecklin [2], Meyer and Jacobson [3], and others obtained the hydrocarbon by the reaction of benzene and anhydrous aluminum chloride on tribom- or trichlor-hydrin. Their product was a thick yellow oily liquid which boiled above 340 degrees C., and could only be distilled under reduced pressure without decomposition. It was thought best to first prepare this compound by the last mentioned method, and then prepare it by use of the Grignard reaction, ftrst preparing the carbinol and reduction to the hydrocarbon. Nothing can be found in the literature where triphenylprorane has been formed by the use of magnesium alkyl halid condensation, so the method used in the formation of tertiary alcohols was followed. [From introductory section]