Organic Lab Reactions 152

Organic Lab Reactions 152 - lecular anhydride of the type...

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CYCLIZATION OF ANHYDRIDES 147 A more generally useful procedure may be developed by preparing the acid chloride according to Procedure II and conducting the cyclization as in Procedure III. ' ' Directions for using nitrobenzene as the cyclizing solvent have been described in detail. 90 The manipulation may be facilitated by the fact that aluminum chloride is soluble in nitrobenzene and can therefore be added in solution. The average yield of ketone on ring closure of 7-3- acenaphthylbutyric acid by this method was 74%. Cyclization of Anhydrides. Instead of the acid chloride, an intramo-
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Unformatted text preview: lecular anhydride of the type LXXIX may be used for cyclization by the Friedel-Crafts reaction (Table VII, examples marked by "h"). This resembles the intermolecular acylation with succinic anhydride, and a similar procedure is generally followed. The product of ring closure is a keto acid LXXX. Nitrobenzene * 66> 120 is a generally effective solvent for the reaction; sym-tetrachloroethane also may be used. 121 COjH LXXX 120 Haworth and Sheldnek, / . Chem. Soc., 1935, 636. 121 Newman and Joshel, J. Am. Chem Soc., 62, 972 (1940)...
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