Synthesis of substituted dinitrophenylketones and phenyl-acetic acids – Part I

| January 9, 1947 | 0 Comments

A.B. Sen & P. M. Bhargava

Published in: Journal of the Indian Chemical Society, 1947, 24, 268-270

Abstract:

2: 4-Dinitro-6-bromophenylacetone and 2: 4-dinitro-6-bromophenylacetic acid have been prepared by the ketonic and acid hydrolysis respectively of the product obtained by the condensation of 1-chloro-2 :4-dinitro-6-bromobenzene with ethyl acetoacetate. The ketone has been characterised by the preparation of suitable derivatives. The reduction of 2: 4-dinitro- 6-bromophenylacetic ester by tin and hydrochloric acid gave rise to an indole derivative.

The simple aromatic halogen compounds like chlorobenzene, do not react with the monosodium derivatives of acetoacetic or malonic ester, as the halogen atom in this case is very firmly fixed to the nucleus. The introduction of negative groups (like nitro), specially in the ortho and para positions to the halogen atom, however, makes it extremely labile and thus facilitates its replacement by various groups. Such compounds can also be condensed with acetoacetic or malonic ester. Considerable work has been done on this subject, the more important contributions being those of Richter (Ber., 1888, 21, 2473), Heckmann (Annalen, 1884:, 220, 137), Jackson (Ber ., 1889, 22, 1232), Reissert and Heller (Ber., 1904, 37, 4634), Borsche (Ber., 1909, 42, 601), Hantzsch and Picton (Ber., 1909, 42, 2126), Borsche and Rantscheff (Annalen, 1911, 379, 180), Borsche Bahr (ibid., 1914:, 402, 91), and Dey and Doraiswami (J. Indian Chem. Soc., 1933, 10, 309).

The esters obtained as above by the condensation of the polynitro halogen compounds with acetoacetic or malonic ester also undergo ketonic and acid hydrolysis and thus provide a suitable method for the preparation of substituted phenylketones and phenyl acetic acids.

In the present paper this reaction has been extended to 1-chloro-2 :4-dinitro-6-bromobenzene with the object of obtaining the appropriate phenylacetone (which has been further characterised by the preparation of the phenylhydrazone and oxime) and phenylacetic acid. The reduction of 2: 4:-dinitro-6- bromophenylacetoacetic ester by tin and hydrochloric acid, which yields an indole derivative, has also been carried out during the course of the work.

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Synthesis of substituted dinitrophenylketones and phenyl-acetic acids – Part I.  A B  SEN & P M BHARGAVA.  Journal of the Indian Chemical Society, 1947, 24, 268-270.

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