THE FRIEDEL-CRAFTS METHOD 131 time resulted in a decrease in yield and increase in formation of high-boning oxygen-containing substances and tars. Dypnone, C6H 6 C(CH 3 )=CHCOC6H 5 , formed by condensation of two molecules of acetophenone was the chief by-product and became essentially the main product when the ketone was present in greater molar quantities than the aluminum chloride. In the reaction of acetyl chloride and toluene under the influence of a variety of catalysts, it was shown M in several instances that a rapid decrease in yield resulted as the reac-tion time was increased. Similarly, low yields of hydrindone-1 (LXXVII) were obtained from /3-phenylpropionyl chloride (LXXVI) and aluminum chloride when the reaction mixture was heated too long. 68 A high-boiling oily substance was the main product, which has been shown 6e to contain some hydrin-denylidenehydrindone-1 (LXXVIII). The chlorine-containing com-pound C 18 Hi 5 0Cl isolated by Kipping 66 may therefore be the product
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