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Synthesis of new safrol derivatives by modifying the side chain

Đang chuẩn bị nút TẢI XUỐNG, xin hãy chờ

Safrol is a natural product, and presents especially in Sassafras oil with 80% abundance. Sassafras oil has been used for long time for treatment of some diseases such as influenza, trouble digestion, stomach and arthritis [1]. Otherwise, Sassafras oil was also used in food and cosmetic industries. Some derivatives of safrol such as heliotropin is a precious perfume used widely in cosmetic industry. Heliotropin was prepared by oxidation of isosafrol [2, 3]. | Joural of Chemistry Vol. 45 3 P. 353 - 355 2007 SyNTHESIS OF NEW SAFROL DERIVATIVES By MODIFyING THE SIDE CHAIN Received 20 April 2006 TRAN VAN Loc TRAN VAN SUNG Institute of Chemistry Vietnamese Academy of Science and Technology SUMMARy By modifying the side chain with different eights derivatives of safrol have been synthesized functional groups. All obtained compounds are new and their structures are assigned by mass analysis and NMR spectra. I - INTRODUCTION Safrol is a natural product and presents especially in Sassafras oil with 80 abundance. Sassafras oil has been used for long time for treatment of some diseases such as influenza trouble digestion stomach and arthritis 1 . Otherwise Sassafras oil was also used in food and cosmetic industries. Some derivatives of safrol such as heliotropin is a precious perfume used widely in cosmetic industry. Heliotropin was prepared by oxidation of isosafrol 2 3 . The exploitation and employing of safrol is limited so far. The synthesis of safrol derivatives bearing the active function groups on the side chain is necessary. These derivatives could be transformed to other compounds which are useful for the research of biologically active molecules. In our previous paper we described the synthesis of several new safrol derivatives containing nitrogen atom 4 . Herein we present the synthesis of some safrol derivatives by modifying on the side chain. II - EXPERIMENTAL Synthesis of 2 and 3 To a solution of 100 ml formic acid containing 0.12 mol of 30 H2O2 solution was added 0.1 mol 16.2 g of safrol at 0oC. The temperature was kept below 20oC. The reaction solution was stirred at the same temperature for 24 h. The formic acid was removed under diminished pressure. The remaining was neutralized with aqueous 5 NaOH solution and then extracted with ethyl acetate 4 times . The combined organic extract was dried over Na2SO4 and the solvent was removed under diminished pressure. The crud was purified by column chromatography on .

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