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

A.B. Sen & P. M. Bhargava

Published in: Journal of the Indian Chemical Society, 1948, 25, 409-404

Abstract:

2:4-Dinitro-6-chlorophenylacetone and 2:4-dinitro- 6-chlorophenylacetic acid have been prepared by the ketonic and acid hydrolysis of 2 :4-dinitro-6-chlorophenylacetoacetic ester. The ketone has been characterised by preparation of suitable derivatives. The reduction of 2:4 dinitro-6-chlorophenylacetoacetic ester by iron powder and water has also been carried out.

In the previous communications (J. Indian Chem. Soc., 1947, 24, 268, 371; 1948, 25, 282), 1-chloro-2:4-dinitro-6-bromobenzene, 1-chloro-2:6-dinitro-4-bromobenzene and 1-chloro-2:4-dinitro-6-iodobenzene have -been condensed with acetoacetic ester and malonic ester, yielding the corresponding substituted acetoacetic and malonic esters, which on ketonic and acid hydrolysis yielded the corresponding phenylacetones and phenylacetic acids respectively. In this paper this reaction has been extended to 1:6- dichloro-2:4-dinitrobenzene. 2:4-Dinitro-6 chlorophenylacetoacetic ester has also been reduced with iron powder and water to an indole derivative.

HOW TO CITE

Synthesis of substituted dinitrophenylketones and phenyl-acetic acids – Part IV. A B SEN & P M BHARGAVA. Journal of the Indian Chemical Society, 1948, 25, 409-404.

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