Aluminum Chloride Catalyzed Reaction of Acetanilide with Pivalyl Chloride

Przemyslaw Maslak, Phillip E. Fanwick, Robert D. Guthrie

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Abstract

Product development was studied in the aluminum chloride catalyzed reaction of acetanilide with pivalyl chloride. 3-tert-Butylacetanilide is the major product because of its relative resistance to dealkylation by reaction-produced HCl. At long reaction times all alkylation products are converted back to acetanilide with the only survivor being 2,2-dimethyl-5-tert-butyl-7-acetamidoindanone. The crystal structure of this compound was determined. It crystallized in the space group Pnmawith cell constants a = 12.571 (3) Á, b = 7.302 (1) Å, c = 16.910 (3) Å, V = 1552.24 Å3, z = 4. Refinement of the 1224 data with F2⩾ 3σF2) resulted in discrepancy indices R1= 0.056 and R2= 0.074. A novel mechanism for formation of this indanone is proposed, involving nucleophilic attack by alkene on a protonated arene ring.

Original languageEnglish (US)
Pages (from-to)655-659
Number of pages5
JournalJournal of Organic Chemistry
Volume49
Issue number4
DOIs
Publication statusPublished - Jan 1 1984

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All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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