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《Journal of Chemical Engineering of Chinese Universities》 2006-06
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Synthesis of 5-[2-(ethylthio)propyl]-1,3-cyclohexanedione

DAI Li-yan1, FANG Jun1, JIANG Xin-peng1, SHI Yong-gen2, CHEN Ying-qi1, Lü Xiu-yang1 (1. Institute of Pharmaceutical Engineering, Department of Chemical and Biochemical Engineering, Zhejiang University, Hangzhou 310027, China; 2. Shangyu Sanhe Pharmaceuticals Chemical Engineering Co. Ltd. of Zhejiang, Shangyu 312369, China)  
5-[2-(ethylthio)propyl]-1,3-cyclohexanedione, the title compound of this study, is an important intermediate for preparation of 3-hydroxy-cyclohex-2-enones herbicides, such as clethodim, sethoxydim, cloproxydim, etc.. The optimization of the synthesis route and the preparation method of the title compound were studied and the results were described concisely as follows. Firstly, 3-ethylthiobutanal was prepared with high yield by reacting crotonaldehyde with ethanethiol in triethylamine. Secondly, methyl acetoacetate was converted to 6-ethylthiohept-3-en-2-one via three steps, hydrolysis, condensation with 3-ethylthiobutanal and dehydration, then the 6-ethylthiohept-3-en-2-one was cyclocondensed with di-Me malonate by Michael addition and Clasisen condensation, and further via saponification and decarboxylation , the title compound was obtained. The products of each steps and the final title compound obtained were compared with each its own standerd samples and were confirmed by LC/MS.
【CateGory Index】: TQ234.2
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