Synthesis of (Z)-3-Butylidene-4-hydroxyphthalide

Abstract

Abstract: (Z)-3-Butylidene-4-hydroxyphthalide(1)was prepared from 2-formyl-3-methoxy benzoic acid(2).2 was converted to 2-pentenyl-3-methoxybenzoic acid(4)by the usual method.4 was dissolved in sodium bicarbonate solution and reacted with a solution of iodine in aqueous potassium iodide to give 5 and 6,which was converted to 3-propyl-5-hydroxyiso coumarine(3)by the conventional method.Iodophthalide(5)was treated with sodium acetate to furnish(Z)-3-butylidene-4-methoxyphthalide(7).Demethylation of 7 was conducted with boron tribromide to give the title compound(1).The overall yield of 1 is 46%.

Key words: (Z)-3-Butylidene-4-hydroxyphthalide, Phthalide, 3-Propyl-5-hydroxyiso-Coumarin, Isocoumarin, Synthesis

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LI Shao-Bai, WANG Zhi-Wei, FANG Xiao-Ping, LI Yu-Lin. Synthesis of (Z)-3-Butylidene-4-hydroxyphthalide[J]. Chem. J. Chinese Universities, 1995, 16(4): 582.

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Synthesis of (Z)-3-Butylidene-4-hydroxyphthalide

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