SYNTHESIS OF MESOTRIONE

The present disclosure relates to a process for synthesis of mesotrione. The process comprises reacting 4-toluene sulfonyl chloride with alkali metal sulphite and alkali metal bicarbonate to obtain alkali metal toluene-4-sulfinate. The alkali metal toluene-4-sulfinate is reacted with alkali metal sa...

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Hauptverfasser: Jain, Nandkumar Janardan, Sathe, Shekhar Vishwanath, Damania, Pragnesh Dalpatram, Mathur, Suchet Saran, Gharda, Keki Hormusji
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creator Jain, Nandkumar Janardan
Sathe, Shekhar Vishwanath
Damania, Pragnesh Dalpatram
Mathur, Suchet Saran
Gharda, Keki Hormusji
description The present disclosure relates to a process for synthesis of mesotrione. The process comprises reacting 4-toluene sulfonyl chloride with alkali metal sulphite and alkali metal bicarbonate to obtain alkali metal toluene-4-sulfinate. The alkali metal toluene-4-sulfinate is reacted with alkali metal salt of monochloroacetic acid to obtain 4-methylsulfonyl toluene. Further, 4-methylsulfonyl toluene is nitrated to obtain 2-nitro-4-methylsulfonyl toluene. 2-nitro-4-methylsulfonyl toluene is oxidized and then halogenated to obtain 2-nitro-4-methylsulfonylbenzoyl halide. 2-nitro-4-methylsulfonylbenzoyl halide is reacted with alkali metal salt of 1,3-cyclohexanedione to obtain 3-(2-Nitro-4-methylsulfonylbenzoyloxy)cyclohexen-1-one which is reacted with base, a third fluid medium and cyanide ion source to obtain an amorphous mesotrione. The present disclosure also discloses the steps of converting the amorphous mesotrione to crystalline mesotrione having purity greater than 99%. The process of the present disclosure for preparing mesotrione is rapid, economic, and environment friendly.
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The process comprises reacting 4-toluene sulfonyl chloride with alkali metal sulphite and alkali metal bicarbonate to obtain alkali metal toluene-4-sulfinate. The alkali metal toluene-4-sulfinate is reacted with alkali metal salt of monochloroacetic acid to obtain 4-methylsulfonyl toluene. Further, 4-methylsulfonyl toluene is nitrated to obtain 2-nitro-4-methylsulfonyl toluene. 2-nitro-4-methylsulfonyl toluene is oxidized and then halogenated to obtain 2-nitro-4-methylsulfonylbenzoyl halide. 2-nitro-4-methylsulfonylbenzoyl halide is reacted with alkali metal salt of 1,3-cyclohexanedione to obtain 3-(2-Nitro-4-methylsulfonylbenzoyloxy)cyclohexen-1-one which is reacted with base, a third fluid medium and cyanide ion source to obtain an amorphous mesotrione. The present disclosure also discloses the steps of converting the amorphous mesotrione to crystalline mesotrione having purity greater than 99%. 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CHEMISTRY
METALLURGY
ORGANIC CHEMISTRY
title SYNTHESIS OF MESOTRIONE
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