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Synthesis of 3-methyleneisobenzofuran-1(3H)-one

Jia Hong-bin

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Abstract

Using methyl o-methylbenzoate as the starting material,o-vinylbenzoic acid was prepared through radical bromination,Wittig reaction and hydrolysis of ester.After epoxidation and cyclization reaction of o-vinylbenzoic acid,3-hydroxymethylisobenzofuran-1(3H)-one was obtained.Then 3-methyleneisobenzofuran-1(3H)-one was synthesized by nucleophilic substitution and elimination reaction of 3-hydroxymethylisobenzofuran-1(3H)-one.The target product didn't dimerize in air over a few weeks.The chemical structures were characterised by 1H NMR,13C NMR and IR.

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What this paper is about

Using methyl o-methylbenzoate as the starting material,o-vinylbenzoic acid was prepared through radical bromination,Wittig reaction and hydrolysis of ester.After epoxidation and cyclization reaction of o-vinylbenzoic acid,3-hydroxymethylisobenzofuran-1(3H)-one was obtained.Then 3-methyleneisobenzofuran-1(3H)-one was synthesized by nucleophilic substitution and elimination reaction of 3-hydroxymethylisobenzofuran-1(3H)-one.The target product didn't dimerize in air over a few weeks.The chemical structures were characterised by 1H NMR,13C NMR and IR.

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Available abstract

Using methyl o-methylbenzoate as the starting material,o-vinylbenzoic acid was prepared through radical bromination,Wittig reaction and hydrolysis of ester.After epoxidation and cyclization reaction of o-vinylbenzoic acid,3-hydroxymethylisobenzofuran-1(3H)-one was obtained.Then 3-methyleneisobenzofuran-1(3H)-one was synthesized by nucleophilic substitution and elimination reaction of 3-hydroxymethylisobenzofuran-1(3H)-one.The target product didn't dimerize in air over a few weeks.The chemical structures were characterised by 1H NMR,13C NMR and IR.

Key concepts: Chemistry, Halogenation, Hydrolysis, Nucleophilic substitution, Wittig reaction, Nucleophile, Acid hydrolysis, Organic chemistry

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