Chinese Journal of Organic Chemistry >
Synthesis of 3-Methyleneisobenzofuran-1(3H)-one and Their Derivatives
Received date: 2012-06-30
Revised date: 2012-08-30
Online published: 2012-08-31
Starting from 2-vinylbenzoic acid methyl ester and derivatives, 3-hydroxymethylisobenzofuran-1(3H)-one and derivatives were prepared through hydrolysis of esters, followed by epoxidation with m-chloroperoxybenzoic acid, cyclization reaction catalyzed by p-toluenesulfonic acid; then nucleophilic substitution with phosphorus tribromide or tosyl chloride and elimination reaction, 3-methyleneisobenzofuran-1(3H)-one and their derivatives were synthesized. The yield of tosyl chloride method was higher than phosphorus tribromide method in the nucleophilic substitution and elimination reaction. Ten target products and intermediates are new compounds. Their structures were characterized by 1H NMR, 13C NMR, MS and IR techniques. The target products did not dimerize in air over a few weeks.
Key words： 3-methylereisobenzofuran-1(3H)-one; protoanemonin; derivatives; synthesis
Zhang Jizhen , Wu Jian , Wang Yazhen , Zhao Dejian , Jia Hongbin . Synthesis of 3-Methyleneisobenzofuran-1(3H)-one and Their Derivatives[J]. Chinese Journal of Organic Chemistry, 2012 , 32(12) : 2344 -2349 . DOI: 10.6023/cjoc201206030
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