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New process for the preparation of 3,5-dihydroxy-1-pentylbenzene

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A new process for the preparation of 3,5-dihydroxy-1-pentylbenzene, which is used as medicinal intermediate and raw material for the synthesis of HIV restrainer, is proposed in this paper. Technical 3,5-dimethoxybenzoic acid reacted with lithium hydride to form a salt (I) which acylated n-butyllithium directly to give 1-(3,5-dimethoxyphenyl)-1-pentanone (II) in 85.06% yield. Then (II) was reduced through a Wolff-K-Huangminglong reaction at 210°C to give 3,5-dimethoxy-1-pentylbenzene (III). Finally, (III) refluxed with melt pyridine hydrochloride at 200°C for 2 h to afford the target product 3,5-dihydroxy-1-pentylbenzene (IV). The total yield of (IV) amounted to 61.50% and its mass percentage was 98.22%. The products were characterized by means of IR, 1H-NMR, GC and HLPC-MS. The results indicated that this synthetic route was feasible, characterized by simple process and higher yield, and superior to the published ones.

Affiliations: 1: School of Chemical Engineering, Changchun University of Technology, Changchun, Jilin 130012, P. R. China; Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Chanchun, Jilin 130021, P. R. China; 2: Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Chanchun, Jilin 130021, P. R. China; 3: School of Chemical Engineering, Changchun University of Technology, Changchun, Jilin 130012, P. R. China

10.1163/156856707782565831
/content/journals/10.1163/156856707782565831
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/content/journals/10.1163/156856707782565831
2007-06-01
2016-12-03

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