Processes Catalyzed by Aluminum Chloride

In all of these processes, it is not clear whether the aluminum chloride, the phosphorus pentachloride, or both are the primary chlorinating agents. While phosphorus pentachloride alone in chloroform has been reported9 to produce tetraacetyl-a-D-fructosyl chloride from /3-D-fructose pentaacetate, its action on /3-D-glucose pentaacetate in the absence of 

In 1945 Hurd and Bonner21 utilized the catalytic action of aluminum chloride in a new connection by successfully alkylating aromatic hydro- 

If Reaction (2) occurred at each acetyl group of III before Reaction (1) proceeded, then eight moles of aluminum chloride would be required, plus an additional amount to promote Reaction (1). Acetophenone should be isolable from the benzene layer, and the carbohydrate product, having undergone deacetylation, would be found in the water layer. Actually, Reaction (1) was realized in the presence of only five moles of catalyst, showing that Reactions (1) and (2) occur simultaneously. 

An attempt was made to increase the yield of IV by employing the theoretically required eight moles of catalyst. Instead of IV, m. p. 

Toluene reacted with III and aluminum chloride much as did benzene, except that yields were lower and tar formation more extensive. From the organic layer methyl p-tolyl ketone was isolated, while acetylation of the product from the aqueous layer led to 1,1-di-p-tolyl- 1-desoxy-D-glucitol hydrate (VI). p-/3-D-Glucopyranosyltoluene, structurally 

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