Studies in the Friedel-Crafts reaction: Part VI-Synthesis and intra-, and inter-molecular Friedel-Crafts reaction of 2-methyl-4-phenylpentanedioic anhydride

摘要

2-Methyl-4-phenylpentanedioic acid 4 is prepared by the Michael reaction of methyl methacrylate with ethyl/methyl phenylacetate or benzyl cyanide followed by the hydrolysis of the adduct. The reaction has been studied using different bases. 4 is converted to its anhydride 5, which on intermolecular Friedel-crafts reaction with AlCl_3 gives 2-methyl-1-tetralone-4-carboxylic acid while its reaction with aryl ethers in the presence of AlCl_3 gives a series of 5-aryl-4-methyl-5-oxo-2-phenylpentanoic acid 8.