Synthesis of 3-Butylidene-5-hydroxyphthalide

Abstract

Abstract: 3-Butylidene-5-hydroxyphthalide (1), isolated from Ligusticum wallichii., hasbeen first syntheslzed starting from 4-hydroxybenzoic acid in 8 steps.Herein compound 4 ondirected matallation with n-butyllithium in the presence of TMEDA followed by treatmentwith DMFgave 5 in 80% yield.The hydrolysis of 5 by employing 4 mol HCl aq.gave 6 in 83% yield.Compound 6 was converted to the acid (7) by the conventional method.Com-pound 7 was dissolved in sodium bicarbonate and reacted with a solution of iodine in aqueouspotassium iodide to give 8.Iodophthalide (8) was reacted with sodium acetate in refluxingethanol to furnish 9 in 94% yield- Demethylation of 9 was conducted in methylene chloridewith boron tribromide to give the title compound(1).The spectral data of 1 are consistentwith those of the natural product.

Key words: (Z)-3-Butylidene-5-hydroxyphthal, Phthalide, Synthesis

CLC Number:

O621.3

TrendMD:

LI Shao-Bai, WANG Zhi-Wei. Synthesis of 3-Butylidene-5-hydroxyphthalide[J]. Chem. J. Chinese Universities, 1997, 18(12): 1987.

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Synthesis of 3-Butylidene-5-hydroxyphthalide

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