The use of a nitro-group to ensure intermolecular acylation by p-nitrohydrocinnamic acid and p-nitro-γ-phenylbutyric acid

Abstract

The deactivating effect of the nitro-group in p-nitrohydrocinnamic acid (VII) and p-nitro-γ-phenylbutyric acid (VIII) facilitates intermolecular acylation with toluene and anisole to provide the corresponding open-chain ketones in the presence of polyphosphoric acid. Intramolecular acylation of p-nitro-γ-phenylbutyric acid (VIII) in polyphosphoric acid gave 7-nitro-α-tetralone (XI) in low yield.