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This document summarizes the synthesis of piperonyl maleamide from safrole through several steps. Safrole was first isolated from cullilawan oil, then isomerized and oxidized to produce piperonal. Piperonal was then reduced to piperonyl alcohol, which was condensed with maleic anhydride to form piperonyl maleic acid. Finally, piperonyl maleic acid was chlorinated and treated with ammonia to yield the final product, piperonyl maleamide, in 48.2% yield. The purity and structures of the products were characterized using GC, FTIR, 1H NMR and MS.
This document summarizes the synthesis of piperonyl maleamide from safrole through several steps. Safrole was first isolated from cullilawan oil, then isomerized and oxidized to produce piperonal. Piperonal was then reduced to piperonyl alcohol, which was condensed with maleic anhydride to form piperonyl maleic acid. Finally, piperonyl maleic acid was chlorinated and treated with ammonia to yield the final product, piperonyl maleamide, in 48.2% yield. The purity and structures of the products were characterized using GC, FTIR, 1H NMR and MS.
This document summarizes the synthesis of piperonyl maleamide from safrole through several steps. Safrole was first isolated from cullilawan oil, then isomerized and oxidized to produce piperonal. Piperonal was then reduced to piperonyl alcohol, which was condensed with maleic anhydride to form piperonyl maleic acid. Finally, piperonyl maleic acid was chlorinated and treated with ammonia to yield the final product, piperonyl maleamide, in 48.2% yield. The purity and structures of the products were characterized using GC, FTIR, 1H NMR and MS.
Healthy Kainama Departement of Chemistry –FKIP,Pattimura University Ambon
ABSTRACT
It has been done the synthesis of piperonyl maleamide as amide derivatives of
C-9154 antibiotic from safrole. Safrole was isolated from cullilawan oil. The synthesis was started by isomerisation of safrole with KOH in ethanol at reflux for 8 hours, then oxidation of isosafrole with KMnO4 using polysorbate 80 as a catalyst in acid at 40oC for 15 minutes to give piperonal. The further experimental stages were reduction of piperonal followed by condensation of piperonyl alcohol with maleic anhydride and chlorination - ammonolysis of the resulted piperonyl maleic acid. The reduction of piperonal with NaBH4 afforded piperonyl alcohol in 90.7 % yield. Condensation of piperonyl alcohol with maleic anhidryde performed in benzena at 60oC for 6 hours gave 40.8 % piperonyl maleic acid. The amide derivative was synthesized through chlorination of piperonyl maleic acid with SOCl2, followed by ammonolysis to yield 48.2 % piperonyl maleamide. The purity of the products was determined using GC, whereas their structures were elucidated using FTIR, 1HNMR and MS It has been done the synthesis of some esters and amide derivatives of C-9154 antibiotic from safrole. Safrole was isolated from cullilawan oil. The synthesis was started by isomerisation of safrole with KOH in ethanol at reflux for 8 hours, then oxidation of isosafrole with KMnO4 using polysorbate 80 as a catalyst in acid at 40oC for 15 minutes to give piperonal. The further experimental stages were reduction of piperonal followed by condensation of piperonyl alcohol with maleic anhydride and chlorination - ammonolysis of the resulted piperonyl maleic acid. The reduction of piperonal with NaBH4 afforded piperonyl alcohol in 90.7 % yield. Condensation of piperonyl alcohol with maleic anhidryde performed in toluene at 60oC for 6 hours gave 9.6 % piperonyl maleic acid. This reaction gave 40.8 % piperonyl maleic acid when this was carried out in benzene under the similar condition. Esterification of piperonyl maleic acid with ethanol in the presence of H2SO4 afforded ethyl piperonyl maleate in 48,3 %. When p- toluene sulfonic acid was used as the catalyst, ethyl piperonyl maleate was obtained in 77.3 % yield. The amide derivative was synthesized through chlorination of piperonyl maleic acid with SOCl2, followed by ammonolysis to yield 48.2 % piperonyl maleamide. Oxymercuration-demercuration was used for the conversion of safrol to safryl alcohol. Condensation of safryl alcohol with maleic anhydride in benzene gave 26.31 % safryl maleic acid. Esterification of safryl maleic acid with ethanol using p- toluene sulfonic acid as the catalyst yielded 40.84 % ethyl safryl maleate. Chlorination of safryl maleic acid using SOCl2, followed by ammonolysis failed to give safryl maleamide probably due to the existence of relatively great steric barrier in the structure of safryl maleic acid. The purity of the products was determined using GC, whereas their structures were elucidated using FTIR, 1HNMR and MS