Organic Lab Reactions 126

Organic Lab Reactions 126 - - The latter evidently arises...

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MET A DIRECTING GROUPS 121 N0 2 XXV The product, which consisted mainly of starting material, contained, surprisingly, a small amount of /3-p-nitrophenylpropionaldehyde (yield 15%). The resistance of some other acids to ring closure because of the presence of the nitro group has been recorded. 21 The carbonyl group seems to have less influence than the nitro group in hindering intramo- lecular acylation. Thus eyclization of the acid chloride of 7-phenyl- pimelic acid (XXVII) by the Friedel-Crafts method (p. 130) gave two products: the tetralonepropionic acid XXVIII and the diketone XXIX. 22
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Unformatted text preview: - The latter evidently arises from the eyclization of XXVIII, which involves acylation meta to the carbonyl group. O C0 2 H CH 2 CH 2 XXVII C0 2 H CH 2 CH 2 XXVIII XXIX In the eyclization of /3-phenyladipic acid (XXX), the main product was the keto acid XXXI, although a small amount of the diketone XXXII was produced. CO S H CH 2 C00H CHjC0 2 H XXX XXXI XXXII l Ggnon and Hudon, Trans. Roy. Soc. Canada, III, S3, 37 (1939) [C. A., 34, 2837 (1940)]. 41 v. Braun and Weisabach, Ber., 64, 178S (1931). 28 Manske, / . Am. Chem. Soc, 63, 1104 (1931). *...
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